A convenient stereoselective synthesis of substituted alkenes via hydroboration-iodination of alkynes

Zweifel, George; Arzoumanian, Henri; Whitney, Charles C.

doi:10.1021/ja00990a061

Cited by 278 publications

(99 citation statements)

References 16 publications

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“…These vinylboranes evidently have rich possibilities for organic synthesis. Thus, the hydroboration of substituted propargyl chlorides provides the convenient route for terminal allenes were β-haloalkyl boranes 55, are the postulated intermediates, in yields of 64-73% (Scheme 16) [29]. Hydroboration of functional alkynes is also possible, and when the functionality is close to the triple bond, further reaction of the boranes may lead to useful synthetic procedure, [30][31][32] where intermediate 56 is β-chloroalkylborane.…”

Section: Hydroboration Of Acetylenesmentioning

confidence: 99%

“…Alkenylboranes react with halogens [29] or acids [43,44] to undergo 1,2-migration of an alkyl group from boron atom to the α-alkenyl carbon. Halogen induced migration products undergo β-elimination to give highly stereospecific alkenes, and also β-haloalkylboranes 74.…”

Section: Scheme 17mentioning

confidence: 99%

“…The predilection of organoboranes to undergo to presence of excess base, usually sodium hydroxide, gave configurationally inverted alkenes [45], and formed as intermediate β-haloalkyl boranes compounds 76A and 76B (Scheme 23). A major drawback of the iodine induced alkene synthesis is that it utilizes one or two alkyl groups.…”

Section: Intramolecular Transfer Reactions Of Alkenylboranes With Inomentioning

confidence: 99%

“…The reaction of 3,5-dimethylborinane with 1-bromo-1-hyxyne afforded intermediate β-iodoalkylborane 106 (Scheme 34) [45]. Hawthorne [64] and later Brown and Rhodes [65] shown The Zweifel olefin synthesis…”

Section: Synthesis Of Exocyclic Olefinsmentioning

confidence: 99%

“…The Zweifel synthesis in the original form provides a stereospecific synthesis of (Z)-alkenes [45] via β-boryl alkyl iodide complexes 108 and 109 (Scheme 36).…”

Section: Synthesis Of Exocyclic Olefinsmentioning

confidence: 99%

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Boranes in Organic Chemistry 3. α-, β- and γ-Haloalkylboranes: The Perspective Vehicles for Organic Synthesis

2016

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<p>The methods of synthesis of α− and β−haloalkylboranes, including chloration of alkylboronic acid esters, additive bromation and chloration of esters of vinyl- and alkenylboronic acids, addition of bromine to trivinylborazines have been considered. The reactions of radical addition of polyhaloidmethanes to vinylboranes, α− and β−unsaturated boronic esters, B-vinyl-B-arylboronic esters, B-trivinyl-B-triarylborazines were discussed. The hydroboration of acetylenic halogenides of dicycloalkylboranes, which led to halocontaining derivatives of dialkylvinylborane was separately considered. The examples of hydroboration of halogenides of allyl and vinyl types are presented. The reaction of dienic synthesis, which takes place between vinylchloroboranes or vinylboronic esters and tetra- or hexachlorocyclopentadienes has been discussed. The reaction of alkenes and allenes with boron tribromide was described. The Markovnikov and non-Markovnikov hydrobromation of boron vinylderivatives has been envisaged. The approaches to the synthesis of perfluoroalkylboranes on the base of hydroboration of perfluoroalkenes have been discussed. The methods of the synthesis of boronates, containing halogetaryl substituents, have been performed. The reactions of hydroboration of halogenides of allylic and propargylic types by 9-borabicyclononane have been shown. The regio- and stereoselectivity of the reaction has been discussed. The examples of the synthesis of boranes of the norbornene type were presented. The reaction of boroallylilation of allyl- and propargylhalogenides leading to the derivatives of 3-bora-bicyclo[3,3,1]-nonane has been discussed. Some directions of using of haloidalkylboranes in the synthesis have been discussed. The examples of nucleophilic substitution leading to oxyalkyl- and azidoalkylboranes have been presented. The route of obtaining of alcohols from α−haloidalkylboranes has been shown. The general scheme of synthesis of α−aminoboronic acids was perfomed. The general approach to the synthesis of allenes on the base of hydroboration products of propargyl halogenides has been discussed. The schemes of synthesis of 1,4-disubstituted-1,2,3-butatrienes are presented. The wide using reaction of introducing of vinylic group into substituent, bonding with boron atom in molecules of dialkylvinylboranes, was discussed. The reactions of new C-C bonds formation, based on the action of iodine on the alkylvinylboronates leading to 1,3-dienes and alkylidencyclanes have been shown. Τhe route of the synthesis of cyclopropanes from β−haloidalkylboranes has been discussed.</p>

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Section: Hydroboration Of Acetylenesmentioning

confidence: 99%

Section: Scheme 17mentioning

confidence: 99%

Section: Intramolecular Transfer Reactions Of Alkenylboranes With Inomentioning

confidence: 99%

Section: Synthesis Of Exocyclic Olefinsmentioning

confidence: 99%

“…The Zweifel synthesis in the original form provides a stereospecific synthesis of (Z)-alkenes [45] via β-boryl alkyl iodide complexes 108 and 109 (Scheme 36).…”

Section: Synthesis Of Exocyclic Olefinsmentioning

confidence: 99%

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