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Journal articles on the topic 'Secondary alkyl halide'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Wang, Bo, Yijing Dai, Weiqi Tong, and Hegui Gong. "Ni-catalyzed reductive addition of alkyl halides to isocyanides." Organic & Biomolecular Chemistry 13, no. 47 (2015): 11418–21. http://dx.doi.org/10.1039/c5ob01901j.

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This work emphasizes Ni-catalyzed reductive trapping of secondary and tertiary alkyl radicals with both aryl isocyanides affording 6-alkylated phenanthridine in good yields. The employment of carbene ligands represents the examples of generation of alkyl radicals from the halide precursors under Ni-catalyzed reductive conditions.

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2

Yoshikai, Naohiko, and Ke Gao. "Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 419–24. http://dx.doi.org/10.1515/pac-2014-5005.

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Abstract A cobalt–N-heterocyclic carbene catalyst allows ortho-alkylation of aromatic imines with unactivated primary and secondary alkyl chlorides and bromides under room-temperature conditions. The scope of the reaction encompasses or complements that of cobalt-catalyzed ortho-alkylation reactions with olefins as alkylating agents that we developed previously. Stereochemical outcomes of secondary alkylation reactions suggest that the reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing group and the cycloalkyl groups.

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3

Zhao, Wenyi, and Henry J. Shine. "Primary and secondary 5-(alkyloxy)thianthrenium perchlorates. Characterization with 1H NMR spectroscopy, reactions with iodide and bromide ion, and thermal decomposition in solution." Canadian Journal of Chemistry 76, no. 6 (June 1, 1998): 695–702. http://dx.doi.org/10.1139/v98-010.

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A series of 5-(alkyloxy)thianthrenium perchlorates has been made in which the alkyl group is primary (1a-1p) and secondary (2a-2g). Preparations were carried out by reaction of the corresponding alkanol with thianthrene cation radical perchlorate in CH2Cl2 solution followed by precipitation of the perchlorate salt with dry ether. 1H NMR spectroscopy reveals that the presence of a stereogenic center in the alkyl group causes inequivalence in the ordinarily paired protons (e.g., H-4, H-6) of the thianthrenium ring. Reaction of iodide and bromide ion with primary alkyl-group compounds (e.g., methyl, ethyl, propyl, butyl) gave the alkyl halide in very good yield and by a second-order kinetic displacement. The second product was thianthrene 5-oxide (ThO). Rate constants for some of these reactions are reported. Reaction of secondary alkyl group compounds (e.g., 2-propyl, 2-pentyl, 2-hexyl, and 3-hexyl) with iodide ion gave good yields of alkyl iodide but also increasing evidence for a side reaction at the sulfonium sulfur, leading to I2, thianthrene, and secondary alkanol. Decomposition of some compounds at 100°C in solution (acetonitrile or 1,2-dichloroethane) was studied and gave alkene(s) and ThO.Key words: thianthrene cation radical, 5-(alkyloxy)thianthrenium perchlorates.

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4

Maas, Gerhard, Vito A. Fiore, Michael Keim, and Roland Werz. "Electrophilic ipso-Halocyclization of N-Phenyl-N-triflylpropiolamides Leading to 8-Halo-1-azaspiro[4.5]deca-3,6,9-trien-2-ones." Synthesis 52, no. 10 (February 19, 2020): 1489–97. http://dx.doi.org/10.1055/s-0039-1691733.

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N-Phenyl-N-triflylpropiolamides react with iodine chloride or iodine bromide by an intramolecular electrophilic ipso-halocyclization/nucleophilic halide addition sequence to furnish cyclohexadiene-spiro-γ-lactams. These products can undergo cleavage of the amide bond with primary amines and of the N–Cspiro bond with secondary amines, leading to N-alkyl-2-iodo-3-phenylacrylamides and N-(4-halophenyl)-2-iodo-3-(2-triflylamino)phenylacrylamides, respectively.

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5

Henningsen, Michael C., Sotiris Jeropoulos, and Edward H. Smith. "Nickel-mediated elimination of hydrogen halide from primary and secondary alkyl bromides and iodides. Synthetic aspects." Journal of Organic Chemistry 54, no. 13 (June 1989): 3015–18. http://dx.doi.org/10.1021/jo00274a010.

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6

Alam, Ryan M., and John J. Keating. "Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution." Beilstein Journal of Organic Chemistry 17 (August 2, 2021): 1939–51. http://dx.doi.org/10.3762/bjoc.17.127.

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The indazole scaffold represents a promising pharmacophore, commonly incorporated in a variety of therapeutic drugs. Although indazole-containing drugs are frequently marketed as the corresponding N-alkyl 1H- or 2H-indazole derivative, the efficient synthesis and isolation of the desired N-1 or N-2 alkylindazole regioisomer can often be challenging and adversely affect product yield. Thus, as part of a broader study focusing on the synthesis of bioactive indazole derivatives, we aimed to develop a regioselective protocol for the synthesis of N-1 alkylindazoles. Initial screening of various conditions revealed that the combination of sodium hydride (NaH) in tetrahydrofuran (THF) (in the presence of an alkyl bromide), represented a promising system for N-1 selective indazole alkylation. For example, among fourteen C-3 substituted indazoles examined, we observed > 99% N-1 regioselectivity for 3-carboxymethyl, 3-tert-butyl, 3-COMe, and 3-carboxamide indazoles. Further extension of this optimized (NaH in THF) protocol to various C-3, -4, -5, -6, and -7 substituted indazoles has highlighted the impact of steric and electronic effects on N-1/N-2 regioisomeric distribution. For example, employing C-7 NO2 or CO2Me substituted indazoles conferred excellent N-2 regioselectivity (≥ 96%). Importantly, we show that this optimized N-alkylation procedure tolerates a wide structural variety of alkylating reagents, including primary alkyl halide and secondary alkyl tosylate electrophiles, while maintaining a high degree of N-1 regioselectivity.

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7

Mo, Fanyang, and Guangbin Dong. "Regioselective ketone α-alkylation with simple olefins via dual activation." Science 345, no. 6192 (July 3, 2014): 68–72. http://dx.doi.org/10.1126/science.1254465.

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Alkylation of carbonyl compounds is a commonly used carbon-carbon bond–forming reaction. However, the conventional enolate alkylation approach remains problematic due to lack of regioselectivity, risk of overalkylation, and the need for strongly basic conditions and expensive alkyl halide reagents. Here, we describe development of a ketone-alkylation strategy using simple olefins as the alkylating agents. This strategy employs a bifunctional catalyst comprising a secondary amine and a low-valent rhodium complex capable of activating ketones and olefins simultaneously. Both cyclic and acyclic ketones can be mono-α-alkylated with simple terminal olefins, such as ethylene, propylene, 1-hexene, and styrene, selectively at the less hindered site; a large number of functional groups are tolerated. The pH/redox neutral and byproduct-free nature of this dual-activation approach shows promise for large-scale syntheses.

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8

Zhang, Xu, Hong Yi, Zhixiong Liao, Guoting Zhang, Chao Fan, Chu Qin, Jie Liu, and Aiwen Lei. "Copper-catalysed direct radical alkenylation of alkyl bromides." Org. Biomol. Chem. 12, no. 35 (2014): 6790–93. http://dx.doi.org/10.1039/c4ob00813h.

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A copper-catalysed direct radical alkenylation of benzyl bromides and α-carbonyl alkyl bromides has been developed. Compared with recent radical alkenylations which mostly focused on secondary or tertiary alkyl halides, this transformation shows good reactivity towards primary alkyl halides and tertiary/secondary alkyl halides are also tolerated.

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9

Knochel, Paul, Maximilian Hofmayer, Jeffrey Hammann, and Gérard Cahiez. "Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides." Synlett 29, no. 01 (August 30, 2017): 65–70. http://dx.doi.org/10.1055/s-0036-1590891.

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An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C–C bond-forming reactions.

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10

Ye, Shengqing, Tianyi Xiang, Xiaofang Li, and Jie Wu. "Metal-catalyzed radical-type transformation of unactivated alkyl halides with C–C bond formation under photoinduced conditions." Organic Chemistry Frontiers 6, no. 13 (2019): 2183–99. http://dx.doi.org/10.1039/c9qo00272c.

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Recent advances in the metal-catalyzed radical-type transformation of unactivated alkyl halides with C–C bond formation under photoinduced conditions are summarized. Usually, a broad reaction scope is observed including tertiary, secondary, and primary alkyl halides, with good functional group compatibility.

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11

Liu, Yunkui, Bingwei Zhou, Qiao Li, and Hongwei Jin. "Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides." Synthesis 52, no. 22 (August 5, 2020): 3466–72. http://dx.doi.org/10.1055/s-0040-1707229.

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We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

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12

Ohmatsu, Kohsuke, Yukino Furukawa, Mari Kiyokawa, and Takashi Ooi. "Diastereo- and enantioselective phase-transfer alkylation of 3-substituted oxindoles with racemic secondary alkyl halides." Chemical Communications 53, no. 98 (2017): 13113–16. http://dx.doi.org/10.1039/c7cc07122a.

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13

Li, Chengxi, Guolan Xiao, Qing Zhao, Huimin Liu, Tao Wang, and Wenjun Tang. "Sterically demanding aryl–alkyl Suzuki–Miyaura coupling." Org. Chem. Front. 1, no. 3 (2014): 225–29. http://dx.doi.org/10.1039/c4qo00024b.

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14

Khamrai, Jagadish, Saikat Das, Aleksandr Savateev, Markus Antonietti, and Burkhard König. "Mizoroki–Heck type reactions and synthesis of 1,4-dicarbonyl compounds by heterogeneous organic semiconductor photocatalysis." Green Chemistry 23, no. 5 (2021): 2017–24. http://dx.doi.org/10.1039/d0gc03792c.

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We report the synthesis of 1,4-dicarbonyl compounds and substituted alkenes (Mizoroki–Heck type coupling) starting from secondary and tertiary alkyl halides and vinyl acetate or styrene derivatives using visible-light photocatalysis.

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15

Saito, Bunnai, and Gregory C. Fu. "Alkyl−Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature." Journal of the American Chemical Society 129, no. 31 (August 2007): 9602–3. http://dx.doi.org/10.1021/ja074008l.

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16

Boteju, Kasuni C., Arkady Ellern, and Aaron D. Sadow. "Homoleptic organolanthanide compounds supported by the bis(dimethylsilyl)benzyl ligand." Chemical Communications 53, no. 4 (2017): 716–19. http://dx.doi.org/10.1039/c6cc09304c.

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A β-SiH functionalized benzyl anion [C(SiHMe₂)₂Ph]⁻ reacts with early rare earth halides to provide homoleptic tris(alkyl)lanthanides containing secondary interactions in an efficient and high yielding route.

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17

Bennett, MA, and GT Crisp. "Oxidative Addition of Functionalized Alkyl-Halides to Iridium(I) Complexes IrCl(Co)L2 (L = PMe2Ph2>, IrCl(Co)PMe3)." Australian Journal of Chemistry 39, no. 9 (1986): 1363. http://dx.doi.org/10.1071/ch9861363.

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Iridium(I) complexes IrCl (CO)L2 (L = PMePh2, PMe2Ph, PMe3) oxidatively add alkyl bromides RBr bearing electron-withdrawing substituents on the α-carbon atom (R = CH2CO2Et,CH3CHCO2Et,CH3CHCOCH3,C2H5CHNO2) to give octahedrally coordinated alkyliridium (III) complexes IrBrClR (CO)L2, for which 1H and 31P n.m.r . data are reported. In the secondary alkyls, the mutually trans tertiary phosphine ligands are inequivalent, consequently the P-Me resonance is not the usual 1 : 2 : 1 'virtual' triplet. In some cases the pattern is a doublet or a doublet of doublets, similar to that expected for mutually cis tertiary phosphine ligands . In contrast to simple s- alkyliridium (III) complexes, the functionalized s-alkyls do not isomerize under any conditions to the corresponding n-alkyls, and the reverse process does not occur for n-alkyls such as IrBrCl (CH2CH2CO2Et)(CO)(PMe3)2 and IrClI (CH2CH2CN)(CO)(PMe3)2. Diiodomethane and chloroiodomethane readily add to IrCl (CO)L2 to give haloalkyliridium (III) complexes IrClI (CH2Y)(CO)L2(Y = Cl , I). These contain mutually trans tertiary phosphine ligands , although in the case of L = PMe2Ph unstable cis - isomers can be detected. Attempts to form complexes containing Ir - CHBrCH3 or Ir -CH(OC2H5)CH3 by addition of CH3CHBr2 or CH3CHClOC2H5 to IrCl (CO)(PMe3)2 gave only IrBr2Cl(CO)(PMe3)2 and IrHCl2(CO)(PMe3)2, respectively.

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18

Yang, Chu-Ting, Zhen-Qi Zhang, Jun Liang, Jing-Hui Liu, Xiao-Yu Lu, Huan-Huan Chen, and Lei Liu. "Copper-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents." Journal of the American Chemical Society 134, no. 27 (June 26, 2012): 11124–27. http://dx.doi.org/10.1021/ja304848n.

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19

Bansal, Paramjit S., Craig L. Francis, Noel K. Hart, Scott A. Henderson, David Oakenfull, Alan D. Robertson, and Gregory W. Simpson. "Regioselective Alkylation of β-Cyclodextrin." Australian Journal of Chemistry 51, no. 10 (1998): 915. http://dx.doi.org/10.1071/c98064.

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Methodology for preparation of heptakis(2,6-di-O-alkyl)-β-cyclodextrins, heptakis(2-O-alkyl)-β- cyclodextrins, and heptakis(6-O-alkyl)-β-cyclodextrins in substantially purified form has been developed. Treatment of β-cyclodextrin (1) with sodium or barium hydroxide and various alkyl halides in dimethyl sulfoxide or a mixture of dimethyl sulfoxide and N,N-dimethylformamide provided the corresponding heptakis(2,6-di-O-alkyl)-β-cyclodextrins. Treatment of heptakis(6-O-t-butyldimethylsilyl)-β-cyclodextrin (5) with sodium hydroxide and several haloalkanes in dimethyl sulfoxide followed by desilylation provided heptakis(2-O-alkyl)-β-cyclodextrins. Protection of the secondary hydroxy groups of the t-butyldimethylsilyl-β-cyclodextrin (5) as benzyl ethers, followed by desilylation, alkylation, and debenzylation afforded several heptakis(6-O-alkyl)-β-cyclodextrins. Analytical methodology has been developed to characterize all of these compounds, with the homogeneity of the pattern of substitution verified by h.p.l.c. analysis, f.a.b.–mass spectrometry and n.m.r. spectroscopy.

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20

Glorius, Frank. "Asymmetric Cross-Coupling of Non-Activated Secondary Alkyl Halides." Angewandte Chemie International Edition 47, no. 44 (October 20, 2008): 8347–49. http://dx.doi.org/10.1002/anie.200803509.

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21

Ren, Peng, Isuf Salihu, Rosario Scopelliti, and Xile Hu. "Copper-Catalyzed Alkylation of Benzoxazoles with Secondary Alkyl Halides." Organic Letters 14, no. 7 (March 9, 2012): 1748–51. http://dx.doi.org/10.1021/ol300348w.

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22

Florin, T. H. J. "Alkyl halides, super hydrogen production and the pathogenesis of pneumatosis cystoides coli." Gut 41, no. 6 (December 1, 1997): 778–84. http://dx.doi.org/10.1136/gut.41.6.778.

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Background and aims—The colons of patients with pneumatosis cystoides coli produce excessive H2. Exposure to alkyl halides could explain this. Six consecutive patients who had pneumatosis cystoides coli while taking chloral hydrate (1–5+ g/day) are reported. Patients 2 and 3 were investigated after they had ceased chloral hydrate treatment. One produced methane, the other did not. (Pneumatosis cystoides coli patients are non-methanogenic according to the literature.) Both had overnight fasting breath H2 of less than 10 ppm. A literature review disclosed just one patient who was using chloral at the time of diagnosed pneumatosis cystoides coli, but an epidemic of the disease in workers exposed to trichloroethylene.Methods—(i) In vitro experiments with human faeces: chloral or closely related alkyl halides were added to anaerobic faecal cultures derived from four methane-producing and three non-methanogenic human subjects. H2 and CH4gases were measured. (ii) In vivo animal experiment: chloral hydrate was added to drinking water of four Wistar rats, and faecal H2 compared with control rats.Results—Alkyl halides increased H2 up to 900 times in methanogenic and 10 times in non-methanogenic faecal cultures. The Ki of chloral was 0.2 mM. Methanogenesis was inhibited in concert with the increase in net H2. In the rat experiment, chloral hydrate increased H2 10 times, but did not cause pneumatosis.Conclusions—Chloral and trichloroethylene are alkyl halides chemically similar to chloroform, a potent inhibitor of H2 consumption by methanogens and acetogens. These bacteria are the most important H2-consuming species in the colon. It is postulated that exposure to these alkyl halides increases net H2 production, which sets the scene for “counterperfusion supersaturation” and the formation of gas cysts. In recent times, very low prescribing rates for chloral have caused primary pneumatosis cystoides to become extremely rare. As with primary pneumatosis, secondary pneumatosis cystoides, which occurs if there is small bowel bacterial overgrowth distal to a proximally located gut obstruction, is predicted by counterperfusion supersaturation. “Inherent unsaturation” due to metabolism of O2 is a safety factor, which could explain why gas bubbles do not form more often in tissue with high H2 tension.

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23

Tanaka, Jiro, Hiroaki Morishita, Masatomo Nojima, and Shigekazu Kusabayashi. "Reaction of phenyl-substituted allyl-lithiums with secondary alkyl halides. A polar process versus single-electron transfer." Journal of the Chemical Society, Perkin Transactions 2, no. 8 (1989): 1009. http://dx.doi.org/10.1039/p29890001009.

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24

Yang, Chu-Ting, Zhen-Qi Zhang, Jun Liang, Jing-Hui Liu, Xiao-Yu Lu, Huan-Huan Chen, and Lei Liu. "ChemInform Abstract: Copper-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents." ChemInform 44, no. 1 (January 1, 2013): no. http://dx.doi.org/10.1002/chin.201301046.

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25

Hofmann, Nora, and Lutz Ackermann. "meta-Selective C–H Bond Alkylation with Secondary Alkyl Halides." Journal of the American Chemical Society 135, no. 15 (April 8, 2013): 5877–84. http://dx.doi.org/10.1021/ja401466y.

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26

Rudolph, Alena, and Mark Lautens. "Secondary Alkyl Halides in Transition-Metal-Catalyzed Cross-Coupling Reactions." Angewandte Chemie International Edition 48, no. 15 (January 28, 2009): 2656–70. http://dx.doi.org/10.1002/anie.200803611.

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27

Fu, G., N. Strotman, and S. Sommer. "Ni-Catalyzed Coupling of Aryl Trifluorosilanes and Secondary Alkyl Halides." Synfacts 2007, no. 7 (July 2007): 0746. http://dx.doi.org/10.1055/s-2007-968640.

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28

Hall, Dennis G., Jack C. H. Lee, and Jinyue Ding. "Catalytic enantioselective transformations of borylated substrates: Preparation and synthetic applications of chiral alkylboronates." Pure and Applied Chemistry 84, no. 11 (June 8, 2012): 2263–77. http://dx.doi.org/10.1351/pac-con-12-02-04.

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Organoboronic acid derivatives are well-established intermediates for the preparation of alcohols and amines, and in the formation of C–C bonds via different reactions, including homologations, carbonyl allylboration, or transition-metal-catalyzed cross-coupling chemistry. In the past decade, there has been great interest in the development of catalytic enantioselective methods for the preparation of chiral, optically enriched organoboronates as precursors of enantioenriched compounds. While the mainstream strategy remains the late-stage borylation of organic functional groups, our group has focused on an alternate strategy focused on modification of boron-containing substrates. In this way, acyclic and cyclic secondary alkyl- and allyl-boronates were prepared through catalytic enantioselective processes such as [4 + 2] cycloadditions, isomerizations, allylic substitutions, and conjugate additions. The resulting optically enriched boronates have been successfully utilized in the syntheses of complex natural products and drugs. One remaining challenge in the chemistry of secondary alkylboronate derivatives is their cross-coupling, especially with control of stereoselectivity. In this regard, our recent approach featured the conjugate asymmetric borylation of β-boronyl acrylates, providing the first enantioselective preparation of highly optically enriched 1,1-diboronyl derivatives. The chirality of these geminal diboron compounds is conferred through the use of two distinct boronate adducts, which can be coupled chemo- and stereoselectively with a variety of aryl and alkenyl halides under palladium catalysis.

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29

Powell, David A., Toshihide Maki, and Gregory C. Fu. "Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents." Journal of the American Chemical Society 127, no. 2 (January 2005): 510–11. http://dx.doi.org/10.1021/ja0436300.

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Ren, Peng, Isuf Salihu, Rosario Scopelliti, and Xile Hu. "ChemInform Abstract: Copper-Catalyzed Alkylation of Benzoxazoles with Secondary Alkyl Halides." ChemInform 43, no. 29 (June 21, 2012): no. http://dx.doi.org/10.1002/chin.201229134.

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31

Jensen, Anne Eeg, and Paul Knochel. "Nickel-Catalyzed Cross-Coupling between Functionalized Primary or Secondary Alkylzinc Halides and Primary Alkyl Halides." Journal of Organic Chemistry 67, no. 1 (January 2002): 79–85. http://dx.doi.org/10.1021/jo0105787.

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32

Ren, Peng, Oleg Vechorkin, Kim von Allmen, Rosario Scopelliti, and Xile Hu. "A Structure–Activity Study of Ni-Catalyzed Alkyl–Alkyl Kumada Coupling. Improved Catalysts for Coupling of Secondary Alkyl Halides." Journal of the American Chemical Society 133, no. 18 (May 11, 2011): 7084–95. http://dx.doi.org/10.1021/ja200270k.

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33

Hofmann, Nora, and Lutz Ackermann. "ChemInform Abstract: meta-Selective C-H Bond Alkylation with Secondary Alkyl Halides." ChemInform 44, no. 38 (August 30, 2013): no. http://dx.doi.org/10.1002/chin.201338147.

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34

Yamasaki, Yuki, Takaharu Hirayama, Koichiro Oshima, and Seijiro Matsubara. "SN2 Type Hydrolysis of Secondary Alkyl Halides and Sulfonates in Hydrothermal Water." Chemistry Letters 33, no. 7 (July 2004): 864–65. http://dx.doi.org/10.1246/cl.2004.864.

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35

Classon, Björn, Susana Ayesa, and Bertil Samuelsson. "A One-Pot, Solid-Phase Synthesis of Secondary Amines from Reactive Alkyl Halides and an Alkyl Azide." Synlett 2008, no. 1 (January 2008): 97–99. http://dx.doi.org/10.1055/s-2007-990927.

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36

Ren, Peng, Lucas-Alexandre Stern, and Xile Hu. "Copper-Catalyzed Cross-Coupling of Functionalized Alkyl Halides and Tosylates with Secondary and Tertiary Alkyl Grignard Reagents." Angewandte Chemie International Edition 51, no. 36 (July 31, 2012): 9110–13. http://dx.doi.org/10.1002/anie.201204275.

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37

Ren, Peng, Lucas-Alexandre Stern, and Xile Hu. "Copper-Catalyzed Cross-Coupling of Functionalized Alkyl Halides and Tosylates with Secondary and Tertiary Alkyl Grignard Reagents." Angewandte Chemie 124, no. 36 (July 31, 2012): 9244–47. http://dx.doi.org/10.1002/ange.201204275.

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38

Ackermann, Lutz. "Transition-metal-catalyzed direct arylations via C–H bond cleavages." Pure and Applied Chemistry 82, no. 7 (May 2, 2010): 1403–13. http://dx.doi.org/10.1351/pac-con-09-08-17.

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Palladium catalysts allowed for intermolecular direct arylations of heteroarenes with aryl chlorides, tosylates, or mesylates as electrophiles. As an economically attractive alter-native, inexpensive copper catalysts could be employed for regioselective C–H bond aryl-ations of 1,2,3-triazoles. On the contrary, intermolecular C–H bond functionalizations of arenes were accomplished with ruthenium complexes derived from air-stable (heteroatom-substituted) secondary phosphine oxide (HASPO) preligands. Particularly, the use of ruthenium(II) carboxylate complexes enabled broadly applicable direct arylations with inter alia aryl tosylates and phenols, and set the stage for unprecedented intermolecular direct alkylations with unactivated alkyl halides bearing β-hydrogens.

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39

Lamothe, S., K. L. Cook, and T. H. Chan. "Chiral organosilicon compounds in synthesis. Preparation and stereoselective alkylations of silylcinnamyl carbanions." Canadian Journal of Chemistry 70, no. 6 (June 1, 1992): 1733–42. http://dx.doi.org/10.1139/v92-217.

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Silylallyl carbanions of type 13 bearing a chiral lithium complexing substituent remote from silicon can be alkylated regio- and stereoselectively at the α-position by small electrophiles in nonpolar solvents. The regiochemical outcome of the reaction was found to be highly dependent on the size of the incoming electrophile. Secondary alkyl halides react preferentially at the γ-center and good levels of stereoselectivity are still obtained in nonpolar solvents despite the rather long distance between the reacting center and the chiral auxiliary. Transformation of the alkylated allylsilanes into optically active alcohols and carboxylic acids may represent a potential synthetic application of the method.

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40

Jensen, Anne Eeg, and Paul Knochel. "ChemInform Abstract: Nickel-Catalyzed Cross-Coupling Between Functionalized Primary or Secondary Alkylzinc Halides and Primary Alkyl Halides." ChemInform 33, no. 27 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200227067.

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41

Gao, Ke, and Naohiko Yoshikai. "Cobalt-Catalyzed Ortho Alkylation of Aromatic Imines with Primary and Secondary Alkyl Halides." Journal of the American Chemical Society 135, no. 25 (June 17, 2013): 9279–82. http://dx.doi.org/10.1021/ja403759x.

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42

Yoshikai, Naohiko, Ke Gao, and Takeshi Yamakawa. "Cobalt-Catalyzed Chelation-Assisted Alkylation of Arenes with Primary and Secondary Alkyl Halides." Synthesis 46, no. 15 (July 9, 2014): 2024–39. http://dx.doi.org/10.1055/s-0033-1338658.

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43

Zhou, Jianrong (Steve), and Gregory C. Fu. "Cross-Couplings of Unactivated Secondary Alkyl Halides: Room-Temperature Nickel-Catalyzed Negishi Reactions of Alkyl Bromides and Iodides." Journal of the American Chemical Society 125, no. 48 (December 2003): 14726–27. http://dx.doi.org/10.1021/ja0389366.

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44

Zakirova, Gladis, Dmitrii Mladentsev, and Nataliya Borisova. "Palladium-Catalyzed C–P Cross-Coupling between (Het)aryl Halides and Secondary Phosphine Oxides." Synthesis 51, no. 11 (March 18, 2019): 2379–86. http://dx.doi.org/10.1055/s-0037-1610698.

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An efficient procedure for C–P bond formation via the palladium-catalyzed [Pd(OAc)2/dppf/Cs2CO3] reaction between dichloroheterocycles and secondary phosphine oxides was developed. The steric and electronic properties of substituents were varied to establish the scope and limitations of the method developed. By applying these conditions, a variety of new heterocyclic compounds bearing two tertiary phosphine oxides were successfully synthesized in moderate to excellent yields. After adjustments to the reaction conditions [Pd(OAc)2/dippf/t-BuOK], cross-coupling of secondary phosphine oxides with bulky (secondary or tertiary alkyl) substituents on the phosphorus atom was achieved. Extension of the methodology to monohalohetarenes and monohaloarenes was successfully carried out; once again, the steric and electronic properties of the halides were varied widely. The desired reaction occurred in all cases studied, giving high to excellent yields of product regardless of the nature and positions of substituents.

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45

Carnaroglio, Diego, Katia Martina, Giovanni Palmisano, Andrea Penoni, Claudia Domini, and Giancarlo Cravotto. "One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction." Beilstein Journal of Organic Chemistry 9 (November 6, 2013): 2378–86. http://dx.doi.org/10.3762/bjoc.9.274.

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A fast and efficient protocol for the synthesis of N,N'-disubstituted urea derivatives from alkyl halides and primary or secondary amines has been developed. The synthetic pathway combines nucleophilic substitutions and a Staudinger–aza-Wittig reaction in the presence of polymer-bound diphenylphosphine under 14 bar of CO2 pressure and has been performed in a one-pot two-step process. The protocol has been optimized under microwave irradiation and the scale-up experiment has been conducted under conventional conditions in a Parr reactor. The final compounds were isolated after simple filtration in almost quantitative overall yields which makes this procedure facile and rapid to execute.

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46

Nayaka, Sreenivasa, Muthuraj R., Bidhayak Chakraborty, Meghashyama Prabhakara Bhat, Pallavi S.S., Shashiraj K.N., Halaswamy H.M., Dhanyakumara S.B., Dattatraya Airodagi, and Kavitha Haged. "A Potential Bioactive Secondary Metabolites and Antimicrobial Efficacy of Streptomyces thermocarboxydus Strain KSA-2, Isolated from Kali River, Karwar." Current Research in Microbiology and Infection 1, no. 1 (November 2020): 5–13. http://dx.doi.org/10.31559/crmi2020.1.1.2.

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In the present study, an Actinomycetes strain KSA-2 was isolated from freshwater sediment samples of Kali River, Karwar, Karnataka, India. The strain KSA-2 was selected among seven isolates based on primary screening of antimicrobial activity against pathogenic organisms. The morphological physiological and biochemical characterizations were performed, the bioactive secondary metabolites were produced in liquid broth culture and was characterized by UV-Vis. spectroscopy and FTIR spectroscopy. Later, the potent KSA-2 strain was identified by 16S rRNA gene sequencing (1366 bp) and a phylogenetic tree was constructed and the strain KSA-2 was confirmed as Streptomyces thermocarboxydus strain KSA-2. Further, the characterization of methanolic extract by UV-Vis. and FTIR spectroscopy analysis revealed the presence of broad spectrum of antimicrobial and other compounds and alkyl halides, alkenes, sulfoxide, carboxylic acids, alkanes respectively.

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47

Journal, Baghdad Science. "Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone." Baghdad Science Journal 10, no. 2 (June 2, 2013): 449–61. http://dx.doi.org/10.21123/bsj.10.2.449-461.

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In the present work, 9-fluorenone-2-carboxylic acid methyl ester (1) was prepared from 9-fluorenone-2-carboxylic acid and then converted into the acid hydrazide (2). Compound (2), is the key intermediate for the synthesis of several series of new compounds such as substituted 1,3,4-oxadiazole derivatives (3-6) were synthesized from the condensation of different substituted benzoic acids with compound (2) using POCl3 as condensing agent. Treatment of compound (2) with formic acid gave the N-formyl hydrazide (7), which upon refluxing with phosphorous pentoxide in benzene yielded the corresponding 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole (8). Reaction of hydrazide (2) with phenyl isocyanate to give N-phenyl semicarbazide derivative (9), then this compound (9) convert to 5-(9-fluorenone-2-yl)-N-phenyl-1,3,4-oxadiazole-2-amine (10) via intramolecular cyclization by syrup H3PO4. Also the hydrazide (2) was treated with CS2/KOH afforded 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-thiol (11). Compound (11) was used to react with various alkyl halides and secondary amines to give 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-alkyl thiol (12-15) and 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-N-alkyl (16-19) derivatives respectively.

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48

Yang, Chu-Ting, Jun Han, Jun Liu, Yi Li, Fan Zhang, Mei Gu, Sheng Hu, and Xiaolin Wang. "Stereocontrolled C(sp3)–P bond formation with non-activated alkyl halides and tosylates." RSC Advances 7, no. 40 (2017): 24652–56. http://dx.doi.org/10.1039/c7ra02766d.

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49

Langhans, Klaus P., Othmar Stelzer, Jürgen Svara, and Norbert Weferling. "Synthese primärer und sekundärer Phosphane durch selektive Alkylierung von PH3 unter Phasentransferbedingungen / Synthesis of Primary and Secondary Phosphines by Selective Alkylation of PH3 under Phase Transfer Conditions." Zeitschrift für Naturforschung B 45, no. 2 (February 1, 1990): 203–11. http://dx.doi.org/10.1515/znb-1990-0215.

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Primary phosphines, RPH2, may be synthesized selectively by alkylation of phosphine, PH3, with alkyl halides RX (R = Me, Et, n-Bu, 2-Bu, C16H33, CH2=CH–CH2, Ph–CH2, 2-Py–CH2–CH2; X = Cl, Br) and concentrated aqueous KOH as auxilliary base in dimethylsulfoxide as a solvent or in two phase systems employing phase transfer catalysts. Under more rigorous conditions secondary phosphines R2PH (R = Me, n-Bu, CH2=CH–CH2) are also accessible in good yields. Using 1,3-dibromo(chloro)-propane or -butane diprimary phosphines H2P–(CH2)2–CHR–PH2 (R = H, Me) are obtained, while 1,4-dibromopentane in a high yield cyclization reaction leads to 2-methylphospholane (12) with a chiral C-atom in a-position.

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50

Ren, Peng, Lucas-Alexandre Stern, and Xile Hu. "ChemInform Abstract: Copper-Catalyzed Cross-Coupling of Functionalized Alkyl Halides and Tosylates with Secondary and Tertiary Alkyl Grignard Reagents." ChemInform 44, no. 7 (February 12, 2013): no. http://dx.doi.org/10.1002/chin.201307044.

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