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Journal articles on the topic 'Carbonyl halides'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 February 2022

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1

Vizer, S. A., and K. B. Yerzhanov. "Heterocycles Synthesis at Carbonylation of Acetylenic Compounds." Eurasian Chemico-Technological Journal 5, no. 2 (April 5, 2016): 145. http://dx.doi.org/10.18321/ectj294.

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The carbonylation of unsaturated hydrocarbons, alcohols, organic halides and other substrates catalyzed by transition metals, salts of transition metals and organometallic complexes is a wide used synthesis method of new carbonyl, carboxyl and alkoxy carbonyl containing compounds including creation or modificationt of heterocycles. The data about synthesis of heterocycles at carbonylation of acetylenic compounds have been appeared at last 20 years and are demonstrated in our review. Introduction of carbon monoxide in the catalytic reactions of acetylenic compounds permits to obtain in oneput process the diverse heterocycles, having carbonyl, carboxyl or alkoxycarbonyl substitutes or containing these fragments inside of heterocycles.

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2

Thomas, Nicholas C. "Substituted ruthenium carbonyl halides." Coordination Chemistry Reviews 70 (July 1986): 121–56. http://dx.doi.org/10.1016/0010-8545(86)80037-6.

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3

C. Thomas, N. "Substituted osmium carbonyl halides." Coordination Chemistry Reviews 93, no. 2 (March 1989): 225–44. http://dx.doi.org/10.1016/0010-8545(89)80017-7.

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4

Francisco, J. S., and Z. Li. "Dissociation pathways of carbonyl halides." Journal of Physical Chemistry 93, no. 24 (November 1989): 8118–22. http://dx.doi.org/10.1021/j100361a029.

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5

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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6

Nagaki, Aiichiro, Yuta Tsuchihashi, Suguru Haraki, and Jun-ichi Yoshida. "Benzyllithiums bearing aldehyde carbonyl groups. A flash chemistry approach." Organic & Biomolecular Chemistry 13, no. 26 (2015): 7140–45. http://dx.doi.org/10.1039/c5ob00958h.

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7

He, Ying, Qifa Liu, Xiaoyun Ma, and Ming Lu. "Oxidation of Benzyl Halides and Related Compounds to Carbonyl Compounds Using Hydrogen Peroxide Catalysed by Tempo in Water." Journal of Chemical Research 37, no. 1 (January 2013): 22–24. http://dx.doi.org/10.3184/174751912x13545558675784.

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A green and straightforward method for the oxidation of benzyl halides and some related compounds to the corresponding carbonyl compounds is reported using hydrogen peroxide catalysed by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) in water. The corresponding carbonyl compounds were obtained with excellent yields in a short time.

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8

Du, Pan, Jiyang Zhao, Shanshan Liu, and Zhen Yue. "Insights into the nucleophilic substitution of pyridine at an unsaturated carbon center." RSC Advances 11, no. 39 (2021): 24238–46. http://dx.doi.org/10.1039/d1ra03019a.

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9

Zhu, Bolin, Xinwei Huang, and Xiaoting Hao. "Synthesis and structures of doubly-bridged dicyclopentadienyl dinuclear rhenium complexes, and their photochemical reactions with aromatic halides in benzene." Dalton Trans. 43, no. 44 (2014): 16726–36. http://dx.doi.org/10.1039/c4dt02370f.

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10

Liu, Xuan-Yu, Bu-Qing Cheng, Yi-Cong Guo, Xue-Qiang Chu, Weidong Rao, Teck-Peng Loh, and Zhi-Liang Shen. "Iron-mediated highly diastereoselective allylation of carbonyl compounds with cyclic allylic halides." Organic Chemistry Frontiers 6, no. 10 (2019): 1581–86. http://dx.doi.org/10.1039/c9qo00210c.

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11

Zhang, Ling, Xiaoyan Lin, Dayun Huang, Xue Liu, and Xiangmei Wu. "Recent Advances in Triarylmethane Synthesis." Synthesis 52, no. 16 (May 14, 2020): 2311–29. http://dx.doi.org/10.1055/s-0040-1707115.

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Triarylmethanes are important molecules in organic chemistry. This review discusses advances in their synthesis summarized in five categories according to the starting materials: (1) benzyl reagents with different leaving groups, such as benzyl alcohols, ethers, esters, phosphates, sulfones, thioethers, sulfonamide, 1,3-dicarbonyls, and ammonium salts; (2) reactions via para- or ortho-quinone methides; (3) arylation of benzyl halides; (4) C–H activation of methylenes; and (5) reactions of aldehydes or N-tosylhydrazones. Triarylmethane derivatives such as 9-arylxanthenones, 9-arylfluorenes, and aryloxepines are also discussed.1 Introduction2 Benzyl Reagents with Leaving Groups3 Quinone Methide Mediated Reactions4 Arylation of Benzyl Halides5 C–H Activation of Methylene6 Reactions of Carbonyl Compounds7 Conclusions

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12

Urbán, Béla, Máté Papp, and Rita Skoda-Földes. "Carbonylation of Aryl Halides in the Presence of Heterogeneous Catalysts." Current Green Chemistry 6, no. 2 (October 25, 2019): 78–95. http://dx.doi.org/10.2174/2213346106666190321141550.

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Palladium-catalyzed carbonylation in the presence of organic and organometallic nucleophiles serves as a powerful tool for the conversion of aryl/alkenyl halides or halide equivalents to carbonyl compounds and carboxylic acid derivatives. To circumvent the difficulties in product separation and recovery and reuse of the catalysts, associated with homogeneous reactions, supported counterparts of the homogeneous palladium catalysts were developed. The review intends to summarize the huge development that has been witnessed in recent years in the field of heterogeneous carbonylation. A great plethora of supports, organic modifiers on solid surfaces stabilizing metal particles, transition metal precursors, as well as alternative sources for CO was investigated. In most cases, careful optimization of reaction conditions was carried out. Besides simple model reactions, the synthesis of carbonyl compounds and carboxylic acid derivatives from substrates with different functionalities was performed. In some cases, causes of palladium leaching were clarified with detailed investigations. The advantages of immobilized catalysts were shown by several examples. The possibility of catalystrecycling was proved besides proving that metal contamination of the products could often be kept below the detection limit. At the same time, detailed investigations should be carried out to gain a better insight into the real nature of these processes.

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13

De Bruyn, W. J., S. X. Duan, X. Q. Shi, P. Davidovits, D. R. Worsnop, M. S. Zahniser, and C. E. Kolb. "Tropospheric heterogeneous chemistry of haloacetyl and carbonyl halides." Geophysical Research Letters 19, no. 19 (October 1992): 1939–42. http://dx.doi.org/10.1029/92gl02199.

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14

Soukhov, V. Yu, N. P. Fadeev, D. N. Suglobov, and G. E. Kodina. "Data on the application of 99Tcm-carbonyl halides." Nuclear Medicine Communications 20, no. 5 (May 1999): 481. http://dx.doi.org/10.1097/00006231-199905000-00097.

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15

Moreno, Consuelo, María-José Macazaga, Rosa-María Medina, David H. Farrar, and Salomé Delgado. "New Procedure for the Synthesis of (Fulvalene)ditungsten Carbonyl Halides and Cyclopentadienyltungsten Carbonyl Halide Complexes with P-Donor Nucleophiles." Organometallics 17, no. 17 (August 1998): 3733–38. http://dx.doi.org/10.1021/om980180+.

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16

Pye, Dominic R., Li-Jie Cheng, and Neal P. Mankad. "Cu/Mn bimetallic catalysis enables carbonylative Suzuki–Miyaura coupling with unactivated alkyl electrophiles." Chemical Science 8, no. 7 (2017): 4750–55. http://dx.doi.org/10.1039/c7sc01170a.

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A bimetallic system consisting of Cu-carbene and Mn-carbonyl co-catalysts was employed for carbonylative C–C coupling of arylboronic esters with alkyl halides, allowing for the convergent synthesis of ketones.

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17

Pola, Josef, and Josef Vítek. "Laser induced gas phase reaction between chromyl chloride and some polyhalogenoethenes." Collection of Czechoslovak Chemical Communications 55, no. 3 (1990): 682–85. http://dx.doi.org/10.1135/cccc19900682.

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Gas phase reaction between chromyl chloride and some polyhalogenoethenes induced with the radiation of continuous-wave CO2 laser yields carbonyl halides and compounds arising from oxygen donation to alkene and 1,2-rearrangement of halogen.

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18

Wang, Gang, Shutao Sun, Ying Mao, Zhiyu Xie, and Lei Liu. "Chromium(II)-catalyzed enantioselective arylation of ketones." Beilstein Journal of Organic Chemistry 12 (December 19, 2016): 2771–75. http://dx.doi.org/10.3762/bjoc.12.275.

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The chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselective addition of aryl halides to both arylaliphatic and aliphatic ketones with high enantioselectivity in an intramolecular version, providing facile access to enantiopure tetrahydronaphthalen-1-ols and 2,3-dihydro-1H-inden-1-ols containing a tertiary alcohol.

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19

Zuo, Huiping, Zhipeng Liu, Wu Yang, Zhikuan Zhou, and Kin Shing Chan. "User-friendly aerobic reductive alkylation of iridium(iii) porphyrin chloride with potassium hydroxide: scope and mechanism." Dalton Transactions 44, no. 47 (2015): 20618–25. http://dx.doi.org/10.1039/c5dt03845f.

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Alkylation of iridium 5,10,15,20-tetrakistolylporphyrinato carbonyl chloride, Ir(ttp)Cl(CO) (1), with 1°, 2° alkyl halides was achieved to give (ttp)Ir-alkyls in good yields under air and water compatible conditions by utilizing KOH as the cheap reducing agent.

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20

Johnson, Stuart, Ervin Kovács, and Michael F. Greaney. "Arylation and alkenylation of activated alkyl halides using sulfonamides." Chemical Communications 56, no. 21 (2020): 3222–24. http://dx.doi.org/10.1039/d0cc00220h.

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21

Zhu, Yi-Zhong, and Chun Cai. "CuI/1,10-phenanthroline: An efficient Catalyst System for the Cyanation of Aryl Halides." Journal of Chemical Research 2007, no. 8 (August 2007): 484–85. http://dx.doi.org/10.3184/030823407x237812.

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Aryl nitriles have been prepared in good yields from the corresponding aryl halides with potassium hexacyanoferrate(II) using CuI/1,10-phenanthroline as the catalyst system. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and carbonyl substituents.

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22

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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23

de Bruyn, Warren J., Jeffrey A. Shorter, Paul Davidovits, Douglas R. Worsnop, Mark S. Zahniser, and Charles E. Kolb. "Uptake of Haloacetyl and Carbonyl Halides by Water Surfaces." Environmental Science & Technology 29, no. 5 (May 1995): 1179–85. http://dx.doi.org/10.1021/es00005a007.

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24

Bartolo, Nicole, Jacquelyne Read, Elizabeth Valentín, and K. Woerpel. "Reactions of Allylmagnesium Halides with Carbonyl Compounds: Reactivity, Structure, and Mechanism." Synthesis 49, no. 15 (June 28, 2017): 3237–46. http://dx.doi.org/10.1055/s-0036-1588427.

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The additions of allylmagnesium reagents to carbonyl compounds are important methods in synthetic organic chemistry, but the mechanisms of these reactions are likely to be distinct from mechanisms followed by other organomagnesium reagents. Additions to alkyl aldehydes and ketones are likely to be concerted, proceeding through six-membered-ring transition states. These highly reactive reagents appear to react at rates that approach the diffusion limit, so chemoselectivity is generally low. Furthermore, reactions of allylmagnesium halides with carbonyl compounds are unlikely to follow stereochemical models that require differentiation between competing transition states. This Short Review discusses the current state of understanding of these reactions, including the structure of the reagent and unique aspects of the reactivity of allylmagnesium reagents.1 Introduction2 Reactions with Carbonyl Compounds2.1 Reactivity of Allylmagnesium Halides2.2 Selectivity of Addition3 Structure of Allylmagnesium Reagents3.1 Schlenk Equilibrium and Aggregation3.2 Spectroscopic Studies3.3 X-ray Crystallographic Studies3.4 Computational Studies of Structure4 Reaction Mechanism4.1 Substrate-Dependent Mechanisms4.2 Concerted Mechanisms4.3 Single-Electron Transfer Mechanisms4.4 Open, SE2′-Like Transition State4.5 Computational Studies of Mechanism5 Conclusion

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25

Liu, Xuan‐Yu, Bu‐Qing Cheng, Yi‐Cong Guo, Xue‐Qiang Chu, Yong‐Xin Li, Teck‐Peng Loh, and Zhi‐Liang Shen. "Bismuth‐Mediated Diastereoselective Allylation Reaction of Carbonyl Compounds with Cyclic Allylic Halides or Cinnamyl Halide." Advanced Synthesis & Catalysis 361, no. 3 (December 11, 2018): 542–49. http://dx.doi.org/10.1002/adsc.201801297.

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26

Cho, Su-Dong, Yong-Jin Yoon, Jeum-Jong Kim, Deok-Heon Kweon, Ho-Kyun Kim, and Sang-Gyeong Lee. "Conversion of Nucleophilic Halides to Electrophilic Halides: Efficient and Selective Halogenation of Azinones, Amides, and Carbonyl Compounds Using Metal Halide/Lead Tetraacetate." Synlett, no. 2 (2006): 194–200. http://dx.doi.org/10.1055/s-2006-926224.

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27

Katritzky, Alan R., and Jamshed N. Lam. "1-ChIoromethyl-3,5-dimethylpyrazole hydrochloride. A useful synthetic intermediate." Canadian Journal of Chemistry 67, no. 7 (July 1, 1989): 1144–47. http://dx.doi.org/10.1139/v89-172.

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1-Chloromethyl-3,5-dimethylpyrazole hydrochloride readily undergoes nucleophilic displacement with O-, N-, or S-nu-cleophiles. 1-Phenylthiomethyl-3,5-dimethylpyrazole can be lithiated at the CH2 group and reacted with alkyl halides and carbonyl compounds. Desulfurization of the products affords a novel method of preparing N-substituted pyrazoles. Keywords: pyrazole, lithiation, chloromethylazoles, desulfurization.

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28

Utimoto, Kiitiro, and Seijiro Matsubara. "Samarium Diiodide-Mediated Reaction of Organic Halides with Carbonyl Compounds." Journal of Synthetic Organic Chemistry, Japan 56, no. 11 (1998): 908–18. http://dx.doi.org/10.5059/yukigoseikyokaishi.56.908.

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29

Francisco, J. S. "Gas-phase hydrolysis of trifluoromethyl carbonyl halides to trifluoroacetic acid." Journal of Physical Chemistry 96, no. 12 (June 1992): 4894–99. http://dx.doi.org/10.1021/j100191a032.

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30

Li, Z., C. Sheng, H. Qiu, and Y. Zhang. "FERRIC CHLORIDE-CATALYZED DEOXYGENATIVE CHLORINATION OF CARBONYL COMPOUNDS TO HALIDES." Organic Preparations and Procedures International 39, no. 4 (August 2007): 412–15. http://dx.doi.org/10.1080/00304940709458597.

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31

Masuyama, Yoshiro, Akihiro Ito, Mamiko Fukuzawa, Kohji Terada, and Yasuhiko Kurusu. "Carbonyl propargylation or allenylation by 3-haloprop-1-yne with tin(ii) halides and tetrabutylammonium halides." Chemical Communications, no. 18 (1998): 2025–26. http://dx.doi.org/10.1039/a806206d.

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32

Adeppa, K., D. C. Rupainwar, and Krishna Misra. "An improved one-pot cost-effective synthesis of N,N-disubstituted carbamoyl halides and derivatives." Canadian Journal of Chemistry 88, no. 12 (December 2010): 1277–80. http://dx.doi.org/10.1139/v10-138.

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A convenient one-pot procedure is reported for preparing N,N-disubstituted carbamoyl chlorides by using chlorocarbonylsulfenyl chloride as a carbonylating agent. It comprises the reaction of secondary amines with chlorocarbonylsulfenyl chloride in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halides. Insertion of the carbonyl group without using phosgene is the novelty of this method.

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33

Yang, Wenyu, Lu Gao, Ji Lu, and Zhenlei Song. "Chemoselective deoxygenation of ether-substituted alcohols and carbonyl compounds by B(C6F5)3-catalyzed reduction with (HMe2SiCH2)2." Chemical Communications 54, no. 38 (2018): 4834–37. http://dx.doi.org/10.1039/c8cc01163j.

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B(C₆F₅)₃-catalyzed deoxygenation of ether-substituted alcohols and carbonyl compounds has been developed using (HMe₂SiCH₂)₂ as the reductant. This reagent shows distinct superiority over traditional one silicon-centered hydrosilanes, giving the corresponding alkanes in high yields with good tolerance of ethers, aryl halides and alkenes.

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34

Yada, Akira. "Palladium-catalyzed Direct ^|^beta;-Arylation of Carbonyl Compounds with Aryl Halides." Journal of Synthetic Organic Chemistry, Japan 72, no. 10 (2014): 1156–57. http://dx.doi.org/10.5059/yukigoseikyokaishi.72.1156.

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35

Ren, Wei, and Motoki Yamane. "Carbamoylation of Aryl Halides by Molybdenum or Tungsten Carbonyl Amine Complexes." Journal of Organic Chemistry 75, no. 9 (May 7, 2010): 3017–20. http://dx.doi.org/10.1021/jo1002592.

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36

Riera, Victor, and Miguel A. Ruiz. "Tetraethyl diphosphite-bridged binuclear carbonyl derivatives of decacarbonyldimanganese and pentacarbonylmanganese halides." Journal of the Chemical Society, Dalton Transactions, no. 12 (1986): 2617. http://dx.doi.org/10.1039/dt9860002617.

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37

Ren, Wei, and Motoki Yamane. "Palladium-Catalyzed Carbamoylation of Aryl Halides by Tungsten Carbonyl Amine Complex." Journal of Organic Chemistry 74, no. 21 (November 6, 2009): 8332–35. http://dx.doi.org/10.1021/jo901486z.

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38

Bogdanov, V. A., Yu I. Savel'ev, R. N. Shchelokov, and V. A. Piven'. "Reactions of rhenium carbonyl halides in an atmosphere of ionized ammonia." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 36, no. 4 (April 1987): 857–59. http://dx.doi.org/10.1007/bf00962339.

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39

Tsonis, C. P. "Oligocondensation of benzyl chloride catalyzed by group VIIB metal carbonyl halides." Journal of Molecular Catalysis 33, no. 1 (October 1985): 61–64. http://dx.doi.org/10.1016/0304-5102(85)85017-3.

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40

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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41

MASUYAMA, Y., A. ITO, M. FUKUZAWA, K. TERADA, and Y. KURUSU. "ChemInform Abstract: Carbonyl Propargylation or Allenylation by 3-Haloprop-1-yne with Tin(II) Halides and Tetrabutylammonium Halides." ChemInform 30, no. 2 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199902046.

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42

Hashemi, Mohammed M., and Yousef Ahmadi Beni. "Copper(I) Chloride/Kieselguhr: A Versatile Catalyst for Oxidation of Alkyl Halides and Alkyl Tosylates to the Carbonyl Compounds." Journal of Chemical Research 23, no. 7 (July 1999): 434–35. http://dx.doi.org/10.1177/174751989902300715.

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43

Li, Hongqi, and Ian S. Butler. "Infrared Photoacoustic Spectra of the Solid Manganese(I) Carbonyl Halides, Mn(CO)5X and [Mn(CO)4X]2 (X = Cl, Br, I)." Applied Spectroscopy 46, no. 12 (December 1992): 1785–89. http://dx.doi.org/10.1366/0003702924123557.

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Mid- and near-IR photoacoustic (PA) spectra have been measured at room temperature for two series of crystalline manganese(I) carbonyl halides: Mn(CO)5 X and [Mn(CO)4 X]2 ( X = Cl, Br, I). Vibrational assignments are proposed for many of the observed bands. The PA spectra in the near-IR region (4200-3800 cm−1), where the binvary v(CO) overtones and combinations absorb, are useful spectral fingerprints for these organomanganese(I) complexes.

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44

Martins F, Harley Paiva, and Roy E. Bruns. "Infrared vibrational intensities and polar tensors of the carbonyl and thiocarbonyl halides." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 53, no. 12 (October 1997): 2115–28. http://dx.doi.org/10.1016/s1386-1425(97)00142-x.

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45

Keh, Charlene C. K., Chunmei Wei, and Chao-Jun Li. "The Barbier−Grignard-Type Carbonyl Alkylation Using Unactivated Alkyl Halides in Water." Journal of the American Chemical Society 125, no. 14 (April 2003): 4062–63. http://dx.doi.org/10.1021/ja029649p.

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46

Adamczyk, Tobias, Guang-Ming Li, Gerald Linti, Hans Pritzkow, Annekathrin Seifert, and Thomas Zessin. "Chromium, Iron and Cobalt Carbonyl Complexes with Gallium Halides: Synthesis and Structures." European Journal of Inorganic Chemistry 2011, no. 23 (July 5, 2011): 3480–92. http://dx.doi.org/10.1002/ejic.201100281.

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47

Chekotylo, Alexej A., Alexandr N. Kostyuk, Alexandr M. Pinchuk, and Andrej A. Tolmachev. "Reaction of ?-carbonyl substituted 1,3,3-trimethyl-2-methyleneindolines with phosphorus(III) halides." Heteroatom Chemistry 14, no. 1 (2003): 23–28. http://dx.doi.org/10.1002/hc.10060.

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48

Utimoto, Kiitiro, and Seijiro Matsubara. "ChemInform Abstract: Samarium Diiodide Mediated Reaction of Organic Halides with Carbonyl Compounds." ChemInform 30, no. 16 (June 16, 2010): no. http://dx.doi.org/10.1002/chin.199916324.

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49

Moragas, Toni, Arkaitz Correa, and Ruben Martin. "Metal-Catalyzed Reductive Coupling Reactions of Organic Halides with Carbonyl-Type Compounds." Chemistry - A European Journal 20, no. 27 (June 6, 2014): 8242–58. http://dx.doi.org/10.1002/chem.201402509.

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50

FRANCISCO, J. S. "ChemInform Abstract: Gas-Phase Hydrolysis of Trifluoromethyl Carbonyl Halides to Trifluoroacetic Acid." ChemInform 23, no. 38 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199238048.

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