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Journal articles on the topic 'Allyl halides'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 February 2022

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1

Mei, Tian-Sheng, Yue-Gang Chen, Xue-Tao Xu, Kun Zhang, Yi-Qian Li, Li-Pu Zhang, and Ping Fang. "Transition-Metal-Catalyzed Carboxylation of Organic Halides and Their Surrogates with Carbon Dioxide." Synthesis 50, no. 01 (September 13, 2017): 35–48. http://dx.doi.org/10.1055/s-0036-1590908.

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Carbon dioxide is not only an essential component of ‘greenhouse gases’, but also an abundant, renewable C1 feedstock in organic synthesis. The catalytic incorporation of carbon dioxide into value-added chemicals to produce carboxylic acids has received enormous attention. This review summarizes recent developments in the transition-metal-catalyzed carboxylation of organic halides and their surrogates, such as aryl, vinyl, and alkyl halides and pseudohalides.1 Introduction2 Carboxylation of Aryl Halides and Pseudohalides3 Carboxylation of Vinyl Halides and Pseudohalides4 Carboxylation of Benzyl Halides and Pseudohalides5 Carboxylation of Allyl Halides and Pseudohalides6 Carboxylation of Propargyl Halides and Pseudohalides7 Carboxylation of Alkyl Halides and Pseudohalides8 Direct Carboxylation of C–H Bonds9 Conclusions and Perspectives

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2

Peppe, Clovis, and Liérson Borges de Castro. "On the reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) towards organyl halides for the synthesis of organyl phenyl chalcogenides." Canadian Journal of Chemistry 87, no. 5 (May 2009): 678–83. http://dx.doi.org/10.1139/v09-043.

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The reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur, selenium) towards organyl halides (organyl = alkyl, allyl, benzyl, acyl) was examined. A practical one-pot method to prepare organyl phenyl chalcogenides from indium metal and diphenyl dichalcogenide was found. The coupling is fairly broad in scope and generally works better for organyl halides capable to produce stable carbocations.

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3

Wang, Shao-Fang, and John Warkentin. "Alkylation of tert-butyl lithiohydrazones of aldehydes and ketones." Canadian Journal of Chemistry 66, no. 9 (September 1, 1988): 2256–58. http://dx.doi.org/10.1139/v88-358.

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Treatment of the tert-butylhydrazones of formaldehyde, acetaldehyde, and acetone with butyllithium afforded the corresponding tert-butyl lithiohydrazones, which were alkylated with alkyl, allyl, and benzyl halides. Fourteen new tert-butylazo compounds were prepared in yields ranging from 38 to 86%.

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4

Khurana, Jitender M., Sanjay Kumar, and Bhaskara Nand. "Facile reductive dehalogenation of organic halides with nickel boride at ambient temperature." Canadian Journal of Chemistry 86, no. 11 (November 1, 2008): 1052–54. http://dx.doi.org/10.1139/v08-156.

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The hydrodehalogenation of a series of aryl, alkyl, allyl, and benzyl chlorides, bromides, and iodides has been carried out efficiently using nickel boride in methanol at ambient temperature, leading to the corresponding products resulting from hydrogen/halogen exchange.Key words: hydrodehalogenation, reduction, organic halides, sodium borohydride, nickel boride.

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5

Huval, Chad C., and Daniel A. Singleton. "Direct free-radical substitutions on allyl and vinyl halides using alkyl halides/hexabutylditin." Tetrahedron Letters 34, no. 19 (May 1993): 3041–42. http://dx.doi.org/10.1016/s0040-4039(00)93373-2.

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6

Verhé, R., N. De Kimpe, L. De Buyck, D. Courtheyn, L. van Caenegem, and N. Schamp. "Reactivity of Electrophilic Allyl Halides." Bulletin des Sociétés Chimiques Belges 92, no. 4 (September 1, 2010): 371–96. http://dx.doi.org/10.1002/bscb.19830920407.

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7

Karabiyikoglu, Sedef, Alexandre V. Brethomé, Thomas Palacin, Robert S. Paton, and Stephen P. Fletcher. "Enantiomerically enriched tetrahydropyridine allyl chlorides." Chemical Science 11, no. 16 (2020): 4125–30. http://dx.doi.org/10.1039/d0sc00377h.

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Enantiomerically enriched allyl halides are rare due to their configurational lability. Stable piperidine-based allyl chloride enantiomers can be produced via kinetic resolution, and undergo highly enantiospecific catalyst-free substitutions.

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8

Schäfer, Philipp, Mireia Sidera, Thomas Palacin, and Stephen P. Fletcher. "Asymmetric cross-coupling of alkyl, alkenyl and (hetero)aryl nucleophiles with racemic allyl halides." Chemical Communications 53, no. 93 (2017): 12499–511. http://dx.doi.org/10.1039/c7cc07151e.

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9

Hassan, Mohamed Ezeldin. "Palladium-catalyzed cross-coupling reaction of organostannanes with nucleoside halides." Collection of Czechoslovak Chemical Communications 56, no. 9 (1991): 1944–47. http://dx.doi.org/10.1135/cccc19911944.

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A general reaction is described for the synthesis of C-5 substituted nucleosides through the coupling of organostannanes with nucleoside-palladium intermediate derived in situ from 5-iodouridine (or 5-iodo-2’-deoxyuridine) and [PdCl2(PPh3)2]. The reaction was used for the synthesis of C-5 aryl, heteroaryl, vinyl, allyl and alkyl substituted nucleosides.

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10

Musalov, Maxim V., Vladimir A. Potapov, and Svetlana V. Amosova. "Efficient Synthesis of a New Family of 2,6-Disulfanyl-9-Selenabicyclo[3.3.1]Nonanes." Molecules 26, no. 10 (May 11, 2021): 2849. http://dx.doi.org/10.3390/molecules26102849.

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The efficient synthesis of a new family of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonanes in high yields has been developed based on 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion generated from bis-isothiouronium salt of 2,6-dibromo-9-selenabicyclo[3.3.1]nonane. The derivatives of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonane containing alkyl, allyl and benzyl moieties have been prepared in 90–99% yields by nucleophilic substitution of 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion with alkyl, allyl and benzyl halides. The reaction of nucleophilic addition of 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion to alkyl propiolates afforded 2,6-di(vinylsulfanyl)-9-selenabicyclo[3.3.1]nonanes. The conditions for regio- and stereoselective addition of 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion to a triple bond of alkyl propiolates have been found. To date, not a single representative of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonanes has been described in the literature.

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11

Promyslov, V. M., and P. P. Shorygin. "Quantum chemical study of allyl halides." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 38, no. 11 (November 1989): 2341–45. http://dx.doi.org/10.1007/bf01168084.

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12

HUVAL, C. C., and D. A. SINGLETON. "ChemInform Abstract: Direct Free-Radical Substitutions on Allyl and Vinyl Halides Using Alkyl Halides/Hexabutylditin." ChemInform 24, no. 40 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199340135.

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13

Kishali, Nurhan, M. Fatih Polat, Ramazan Altundas, and Yunus Kara. "A Novel One-Pot Conversion of Allyl Alcohols into Primary Allyl Halides Mediated by Acetyl Halide." Helvetica Chimica Acta 91, no. 1 (January 2008): 67–72. http://dx.doi.org/10.1002/hlca.200890014.

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14

Musalov, Maxim V., Vladimir A. Potapov, Vladimir A. Yakimov, Maria V. Musalova, Arkady A. Maylyan, Sergey V. Zinchenko, and Svetlana V. Amosova. "A Regioselective Synthesis of Novel Functionalized Organochalcogen Compounds by Chalcogenocyclofunctionalization Reactions Based on Chalcogen Halides and Natural Products." Molecules 26, no. 12 (June 18, 2021): 3729. http://dx.doi.org/10.3390/molecules26123729.

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The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium dibromide with allyl thymol and allyl carvacrol proceeded in methylene chloride at room temperature in the presence of NaHCO3 affording bis[(7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] and bis[(4-isopropyl-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] selenides in 90–92% yield. Similar sulfides were obtained in 70–72% yields by the reaction of sulfur dichloride in chloroform under reflux. Trihalotellanes containing the same organic moieties were synthesized from allyl thymol, allyl carvacrol and tellurium tetrachloride or tetrabromide in quantitative yields. Corresponding functionalized ditellurides were prepared in 91–92% yields by the reduction of the trichlorotellanes with sodium metabisulfite in two-phase solvent system. The comparison of reactivity of sulfur, selenium and tellurium halides in chalcogenocyclofunctionalization and distinguishing features of each reaction were discussed.

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15

Li, Die, Xin-Xing Wu, Tingyu Gao, Baoguo Li, and Shufeng Chen. "CuCl-Catalyzed direct C–H alkenylation of benzoxazoles with allyl halides." Organic & Biomolecular Chemistry 15, no. 35 (2017): 7282–85. http://dx.doi.org/10.1039/c7ob01838j.

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16

Klečka, Martin, Tomáš Tobrman, and Dalimil Dvořák. "Cu(I)-Catalyzed Coupling of (9-Benzylpurin-6-yl)magnesium Chloride with Allyl Halides: An Approach to 6-Allylpurine Derivatives." Collection of Czechoslovak Chemical Communications 71, no. 8 (2006): 1221–28. http://dx.doi.org/10.1135/cccc20061221.

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6-Allylpurine derivatives are formed by Cu(I)-catalyzed coupling of (9-benzyl-9H-purin-6-yl)- magnesium chloride with allyl halides. The reaction is accompanied by allylic rearrangement in some cases. Under acid conditions the double bond of the allyl group rearranges to the conjugation with purine ring.

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17

Malysheva, Svetlana, Boris Sukhov, Nina Gusarova, Svetlana Shaikhudinova, Tat'yana Kazantseva, Natal'ya Belogorlova, Vladimir Kuimov, and Boris Trofimov. "Phosphorylation of Allyl Halides with White Phosphorus." Phosphorus, Sulfur, and Silicon and the Related Elements 178, no. 3 (March 1, 2003): 425–29. http://dx.doi.org/10.1080/10426500307917.

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18

Kalita, E., and D. Kim. "Interaction of 2,2'-Bipyridine with Allyl Halides." «Bulletin of the South Ural State University series "Chemistry"» 10, no. 1 (2018): 17–24. http://dx.doi.org/10.14529/chem180102.

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19

Li, Fu-sheng, Yu-qing Chen, Shuang-jie Lin, Cai-zhe Shi, Xi-yu Li, Yu-chen Sun, Zhuo-wen Guo, and Lei Shi. "Visible-light-mediated Barbier allylation of aldehydes and ketones via dual titanium and photoredox catalysis." Organic Chemistry Frontiers 7, no. 21 (2020): 3434–38. http://dx.doi.org/10.1039/d0qo00171f.

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This study reports a photocatalytic Barbier-type allylation of various aldehydes and ketones with allyl halides for the synthesis of homoallylic alcohols driven by dual titanium and photoredox catalysis.

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20

Fleury, Lauren M., and Brandon L. Ashfeld. "Generation of allyl Grignard reagents via titanocene-catalyzed activation of allyl halides." Tetrahedron Letters 51, no. 18 (May 2010): 2427–30. http://dx.doi.org/10.1016/j.tetlet.2010.02.144.

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21

Kurosawa, Hideo, Mitsuhiro Emoto, and Yoshikane Kawasaki. "Reductive elimination of η3-allyl(aryl)palladium complexes promoted by allyl halides." Journal of Organometallic Chemistry 346, no. 1 (May 1988): 137–46. http://dx.doi.org/10.1016/0022-328x(88)87011-6.

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22

Dmowski, Wojciech, and Ryszard Wozniacki. "Alkylation of perfluoro-2-methyl-2-pentylcarbanion with alkyl and allyl halides." Journal of Fluorine Chemistry 36, no. 4 (September 1987): 385–94. http://dx.doi.org/10.1016/s0022-1139(00)81980-6.

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23

Potapov, Vladimir A., Roman S. Ishigeev, Lyudmila A. Belovezhets, Irina V. Shkurchenko, and Svetlana V. Amosova. "New Water-Soluble Condensed Heterocyclic Compounds with Antimicrobial Activity Based on Annulation Reactions of 8-Quinolinesulfenyl Halides with Natural Products and Alkenes." Applied Sciences 11, no. 18 (September 14, 2021): 8532. http://dx.doi.org/10.3390/app11188532.

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The annulation reactions of 8-quinolinesulfenyl halides with natural products and alkenes affording new water-soluble [1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives in high or quantitative yields are developed in this study. The reactions with styrene derivatives and terminal alkenes including allyl arenes proceed in a regioselective manner but with the opposite regiochemistry. The reactions with terminal alkenes including allyl arenes occur in an anti-Markovnikov fashion (regarding addition of the 8-quinolinesulfenyl electrophile to the double bond) to give 2-organyl-2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium halides, while the reactions with styrene derivatives proceed in a Markovnikov fashion, leading to 3-substituted condensed heterocyclic compounds. In general, styrene derivatives demonstrate higher reactivity in the annulation reactions compared to the terminal alkenes. Antimicrobial activity of novel water-soluble compounds against Enterococcus durans, Bacillus subtilis and Escherichia coli are evaluated. The compounds with high antimicrobial activity are found. The annulation products of the reactions of 8-quinolinesulfenyl halides with 1H-indene, eugenol, methyl eugenol and 1-heptene, are superior in their activity compared to the antibiotic gentamicin.

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24

Xiao, Zecai, and Ai-Yun Peng. "Palladium(II) Acetate Catalyzed Cyclization–Coupling of (o-Ethynylphenyl)phosphonic Acid Monoesters with Allyl Halides." Synthesis 51, no. 18 (June 12, 2019): 3499–505. http://dx.doi.org/10.1055/s-0039-1689936.

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A Pd(OAc)2-catalyzed tandem cyclization–coupling reaction of (o-ethynylphenyl)phosphonic acid monoesters and allyl halides has been developed. This reaction provides an efficient, mild, general and regioselective way to synthesize 4-allylphosphaisocoumarins.

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25

Verhé, R., R. Thierie, D. Courtheyn, N. De Kimpe, L. De Buyck, and N. Schamp. "The Reactivity of Electrophilic Allyl Halides Towards Nucleophiles." Bulletin des Sociétés Chimiques Belges 91, no. 5 (September 1, 2010): 430. http://dx.doi.org/10.1002/bscb.19820910589.

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26

Zhang, Fang, Ru Wang, San Wu, Peipei Wang, and Songlin Zhang. "Highly α-regioselective neodymium-mediated allylation of diaryl ketones." RSC Advances 6, no. 90 (2016): 87710–18. http://dx.doi.org/10.1039/c6ra18378f.

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The first utility of neodymium as a mediating-metal in the Barbier reaction of diaryl ketones with allyl halides is reported in this paper. This one-pot reaction was highly α-regioselective and was carried out under mild conditions.

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27

Bedford, Robin B., Peter B. Brenner, Emma Carter, Thomas W. Carvell, Paul M. Cogswell, Timothy Gallagher, Jeremy N. Harvey, et al. "Expedient Iron-Catalyzed Coupling of Alkyl, Benzyl and Allyl Halides with Arylboronic Esters." Chemistry - A European Journal 20, no. 26 (April 8, 2014): 7935–38. http://dx.doi.org/10.1002/chem.201402174.

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28

Khan, Arif Ali, Philip Junker, Gregor Schnakenburg, Arturo Espinosa Ferao, and Rainer Streubel. "Competitive or sequential reaction of an electrophilic terminal phosphinidene metal(0) complex with allyl halides? [2+1]-cycloaddition vs. C–X bond insertion." Chemical Communications 55, no. 67 (2019): 9987–90. http://dx.doi.org/10.1039/c9cc05328j.

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Transient terminal phosphinidene complex [(CO)₅WPCH(SiMe₃)₂] reacted with allyl halides (X = F, Cl, Br) to give different products. DFT calculations revealed a novel rearrangement with C → P X atom transfer of transient phosphirane complexes.

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29

El Abbouchi, Abdelmoula, Jamal Koubachi, Nabil El Brahmi, and Said El Kazzouli. "Direct arylation and Suzuki-Miyaura coupling of imidazo[1,2-a]pyridines catalyzed by (SIPr)Pd(allyl)Cl complex under microwave-irradiation." Mediterranean Journal of Chemistry 9, no. 5 (November 27, 2019): 347–54. http://dx.doi.org/10.13171/mjc1911271124sek.

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A short and practical arylation of imidazo[1,2-a]pyridine and imidazole derivatives with aryl halides or aryl boronic acids as coupling partners was successfully carried out using phosphine-free (SIPr)Pd(allyl)Cl as the catalyst [SIPr: (N,N’-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)] ((SIPr)Pd(allyl)Cl complex). 3,6-disubstituted imidazo[1,2-a]pyridine and 5-substituted imidazole compounds were obtained in good to excellent yields in only 1h under microwave-assisted C-H arylation and Suzuki-Miyaura coupling reaction conditions.

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30

Hegedus, Louis S., and David H. P. Thompson. "The reactions of organic halides with (.pi.-allyl)nickel halide complexes: a mechanistic study." Journal of the American Chemical Society 107, no. 20 (October 1985): 5663–69. http://dx.doi.org/10.1021/ja00306a012.

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31

Fleury, Lauren M., and Brandon L. Ashfeld. "ChemInform Abstract: Generation of Allyl Grignard Reagents via Titanocene-Catalyzed Activation of Allyl Halides." ChemInform 41, no. 34 (July 29, 2010): no. http://dx.doi.org/10.1002/chin.201034072.

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32

Moral, Daniel del, Josep M. Moretó, Elies Molins, and Susagna Ricart. "Nickel-catalyzed carbonylative cycloaddition of allyl halides and alkenes." Tetrahedron Letters 49, no. 49 (December 2008): 6947–50. http://dx.doi.org/10.1016/j.tetlet.2008.09.040.

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33

Tanaka, Hideo, Shiro Yamashita, Takeshi Hamatani, Youichi Ikemoto, and Sigeru Torii. "PbBr2Al-Promoted Allylation of Carbonyl Compounds with Allyl Halides." Synthetic Communications 17, no. 7 (May 1987): 789–94. http://dx.doi.org/10.1080/00397918708063934.

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34

De Kimpe, Norbert, Sven Mangelinckx, Dirk Courtheyn, Roland Verhé, Veronique Van Speybroeck, and Michel Waroquier. "Reaction of Electrophilic Allyl Halides with Amines: A Reinvestigation." Synthesis 2006, no. 13 (July 2006): 2260–64. http://dx.doi.org/10.1055/s-2006-942421.

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35

El-Shehawy, Ashraf A. "Allylation of aldiminomercaptotriazinones using allyl halides and allylmetal compounds." Heteroatom Chemistry 14, no. 3 (2003): 280–87. http://dx.doi.org/10.1002/hc.10144.

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36

STADNICHUK, M. D., and E. A. ALEKSANDROVA. "ChemInform Abstract: Reaction of Allyl Halides with Silyl Acetylenes." ChemInform 25, no. 43 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199443100.

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37

Franks, Russell J., and Kenneth M. Nicholas. "Palladium-Catalyzed Carboxylative Coupling of Allylstannanes and Allyl Halides." Organometallics 19, no. 8 (April 2000): 1458–60. http://dx.doi.org/10.1021/om0000966.

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38

Bumagin, N. A., A. B. Ponomarev, and I. P. Beletskaya. "Synthesis of allylacetylenes from terminal acetylenes and allyl halides." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 36, no. 7 (July 1987): 1445–48. http://dx.doi.org/10.1007/bf01557520.

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39

Flid, V. R., V. S. Vasyukov, and A. P. Belov. "Reaction of bis-?3-allylnickel complexes with allyl halides." Theoretical and Experimental Chemistry 26, no. 3 (1990): 348–52. http://dx.doi.org/10.1007/bf00641349.

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40

Dilman, Alexander, Vitalij Levin, Daniil Agababyan, and Marina Struchkova. "Dimerization of Benzyl and Allyl Halides via Photoredox-Mediated Disproportionation of Organozinc Reagents." Synthesis 50, no. 15 (May 23, 2018): 2930–35. http://dx.doi.org/10.1055/s-0036-1591583.

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Benzyl and allyl halides undergo homocoupling when treated with zinc in the presence of a catalytic amount of a cationic iridium(III) complex under irradiation with 400 nm light-emitting diodes. The reaction proceeds through the intermediate formation of an organozinc reagent, which disproportionates to a free radical and elemental zinc under photoredox conditions.

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41

Li, Wanfang, Jie Kang Boon, and Yu Zhao. "Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities." Chemical Science 9, no. 3 (2018): 600–607. http://dx.doi.org/10.1039/c7sc03149a.

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42

Hong, Jong-Tai, and Hye-Young Jang. "Platinum-Catalyzed Diastereoselective Intramolecular Coupling of Allyl Halides and Hydrazones." Journal of Organic Chemistry 76, no. 16 (August 19, 2011): 6877–82. http://dx.doi.org/10.1021/jo200993v.

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43

Cui, Dong-Mei, Naoko Hashimoto, Shin-ichi Ikeda, and Yoshiro Sato. "Nickel-catalyzed cross-coupling reaction of allyl halides with alkynyltins." Journal of Organic Chemistry 60, no. 18 (September 1995): 5752–56. http://dx.doi.org/10.1021/jo00123a006.

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44

Chen, Shufeng, and Jianbo Wang. "Palladium-catalyzed reaction of allyl halides with α-diazocarbonyl compounds." Chemical Communications, no. 35 (2008): 4198. http://dx.doi.org/10.1039/b806970k.

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45

Ho Lee, Phil, Kooyeon Lee, and Sukbok Chang. "In-MEDIATED ALLYLATION OF α-KETO ESTERS WITH ALLYL HALIDES*." Synthetic Communications 31, no. 20 (January 2001): 3189–96. http://dx.doi.org/10.1081/scc-100105896.

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46

Sá, Ana C. P. F. de, Giovanna M. A. Pontes, José A. L. dos Anjos, Sidney R. Santana, Lothar W. Bieber, and Ivani Malvestiti. "Reductive coupling reaction of benzyl, allyl and alkyl halides in aqueous medium promoted by zinc." Journal of the Brazilian Chemical Society 14, no. 3 (May 2003): 429–34. http://dx.doi.org/10.1590/s0103-50532003000300015.

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47

Bandini, Marco, Pier Giorgio Cozzi, and Achille Umani-Ronchi. "Asymmetric synthesis with "privileged" ligands." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 325–29. http://dx.doi.org/10.1351/pac200173020325.

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Different types of chiral "privileged" ligands 1 and 2 in promoting enantioselective addition of allylating agents to aliphatic and aromatic aldehydes are described. Here, a new concept in the asymmetric allylation reaction is presented. Redox [Cr (Salen) ] mediated addition of allyl halides to carbonyl compounds is described, and mechanistic investigations are discussed. These results open access to the fascinating area of the catalytic redox processes mediated by metallo-Salen complexes.

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48

Ye, Fei, Mohammad Lokman Hossain, Yan Xu, Xiaoshen Ma, Qing Xiao, Yan Zhang, and Jianbo Wang. "Synthesis of Allyl Allenes through Three-Component Cross-Coupling Reaction ofN-Tosylhydrazones, Terminal Alkynes, and Allyl Halides." Chemistry - An Asian Journal 8, no. 7 (April 24, 2013): 1404–7. http://dx.doi.org/10.1002/asia.201300340.

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49

Zhang, Songlin, Dengbing Xie, Yiqiong Wang, and Bo Yang. "Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite." Synthesis 52, no. 22 (August 12, 2020): 3446–51. http://dx.doi.org/10.1055/s-0040-1707219.

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The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

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Cao, Xu yan, Fei Huang, and Songlin Zhang. "An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite." Synlett 30, no. 12 (June 25, 2019): 1437–41. http://dx.doi.org/10.1055/s-0039-1690096.

Full text

Abstract:

The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.

APA, Harvard, Vancouver, ISO, and other styles

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