Vinyl halide: Difference between revisions
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Kingkoh1987 (talk | contribs) m Added olefin metathesis as a new way to generate vinyl halides efficiently and stereoselectively. |
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Vinyl halides are very useful synthetic intermediates due to the vast number of reactions that make use of them. These include conversion to vinyl [[Grignard reaction|Grignard reagents]], elimination to give the corresponding [[alkyne]], and most importantly their use in [[coupling reaction|cross-coupling reactions]] (e.g. [[Suzuki reaction|Suzuki-Miyaura coupling]], [[Stille reaction|Stille coupling]], [[Heck reaction|Heck coupling]], etc.). |
Vinyl halides are very useful synthetic intermediates due to the vast number of reactions that make use of them. These include conversion to vinyl [[Grignard reaction|Grignard reagents]], elimination to give the corresponding [[alkyne]], and most importantly their use in [[coupling reaction|cross-coupling reactions]] (e.g. [[Suzuki reaction|Suzuki-Miyaura coupling]], [[Stille reaction|Stille coupling]], [[Heck reaction|Heck coupling]], etc.). |
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As a result, there is a large number of reactions to form vinyl halides, which includes the reaction of vinyl [[organometallic]] species with halogens, and the [[Takai olefination|Takai]] and [[Wittig reaction|Wittig olefination]] reactions. |
As a result, there is a large number of reactions to form vinyl halides, which includes the reaction of vinyl [[organometallic]] species with halogens, and the [[Takai olefination|Takai]] and [[Wittig reaction|Wittig olefination]] reactions. Recently, olefin metathesis has been shown to offer a distinct synthesis approach to access vinyl halides efficiently and stereoselectively.<ref>{{Cite journal|last = Koh|first = Ming Joo|last2 = Nguyen|first2 = Thach T.|last3 = Zhang|first3 = Hanmo|last4 = Schrock|first4 = Richard R.|last5 = Hoveyda|first5 = Amir H.|title = Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis|url = http://www.nature.com/doifinder/10.1038/nature17396|journal = Nature|volume = 531|issue = 7595|pages = 459–465|doi = 10.1038/nature17396}}</ref> |
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Besides, some vinyl halides are useful for synthesizing [[polymer]]s and [[copolymer]]s, see e.g. [[polyvinyl chloride]] or [[polyvinyl fluoride]]. The unsubstituted vinyl halides (R<sub>1</sub> = R<sub>2</sub> = R<sub>3</sub> = H) may polymerize spontaneously under certain conditions. |
Besides, some vinyl halides are useful for synthesizing [[polymer]]s and [[copolymer]]s, see e.g. [[polyvinyl chloride]] or [[polyvinyl fluoride]]. The unsubstituted vinyl halides (R<sub>1</sub> = R<sub>2</sub> = R<sub>3</sub> = H) may polymerize spontaneously under certain conditions. |
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Revision as of 16:13, 27 March 2016
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In organic chemistry, a vinyl halide is any alkene with at least one halide substituent bonded directly on one of the alkene carbons. Vinyl chloride is one such substance.
Vinyl halides are very useful synthetic intermediates due to the vast number of reactions that make use of them. These include conversion to vinyl Grignard reagents, elimination to give the corresponding alkyne, and most importantly their use in cross-coupling reactions (e.g. Suzuki-Miyaura coupling, Stille coupling, Heck coupling, etc.).
As a result, there is a large number of reactions to form vinyl halides, which includes the reaction of vinyl organometallic species with halogens, and the Takai and Wittig olefination reactions. Recently, olefin metathesis has been shown to offer a distinct synthesis approach to access vinyl halides efficiently and stereoselectively.[1]
Besides, some vinyl halides are useful for synthesizing polymers and copolymers, see e.g. polyvinyl chloride or polyvinyl fluoride. The unsubstituted vinyl halides (R1 = R2 = R3 = H) may polymerize spontaneously under certain conditions.
 | This article about an organic halide is a stub. You can help Wikipedia by expanding it. |
- ^ Koh, Ming Joo; Nguyen, Thach T.; Zhang, Hanmo; Schrock, Richard R.; Hoveyda, Amir H. "Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis". Nature. 531 (7595): 459–465. doi:10.1038/nature17396.