Aryl and vinyl cyclopropanes through the in situ generation of B-cyclopropyl-9-BBN and its Suzuki–Miyaura coupling

Soderquist, John A.; Huertas, Ramon; Leon‐Colon, Gisela

doi:10.1016/s0040-4039(00)00605-5

Cited by 26 publications

(13 citation statements)

References 21 publications

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“…Initial work by the groups of Marsden, [12] Charette, [13,14] Deng, [15][16][17][18][19][20][21][22] and Soderquist [23] revealed that geometrically pure (racemic) cyclopropylborons could be coupled under palladium(0) catalysis with a broad array of activated coupling partners in good yields and complete retention of configuration (Table 1). Both boronic esters (entries 1-3), boronic acids (entries 4-8), potassium trifluoroborate salts (entry 9), and boranes (entry 10) could be used with sp 2 -based and activated sp 3 -based electrophiles.…”

Section: Couplings Of Cyclopropyl Boronic Estersmentioning

confidence: 99%

Stereospecific Couplings of Secondary and Tertiary Boronic Esters

2014

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Section: Couplings Of Cyclopropyl Boronic Estersmentioning

confidence: 99%

Stereospecific Couplings of Secondary and Tertiary Boronic Esters

2014

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“…Soderquist et al have reported the hydroxy(cyclopropyl)-9-BBN complex 239, which undergoes an efficient crosscoupling reaction under mild conditions to produce a variety of aryl-and vinylcyclopropanes in good to excellent yield (Scheme 109). 254 In general, the participation of n-alkylboronic acid esters in the SM cross-couplin g reaction is rare and the yields of the reaction are normally low. Recently, Molander and Ito have illustrated the cross-coupling of potassium n-alkyltrifluoroborates with aryl and alkenyl triflates.…”

Section: Coupling Of Sp 3 Hybridised C -B Compoundsmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,635

530

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“…Matos and Soderquist [77] using propargyl bromide for dihydroboration with 9-BBN-H followed by treatment of the adduct with aqueous sodium hydroxide obtained the hydroxy(cyclopropyl)borate complexes, which underwent efficient palladiumcatalyzed cross-coupling to produce a variety of aryl and vinyl cyclopropanes in good to excellent yields via formation of γ-bromoalkylborane 146 [78].…”

Section: Scheme 50mentioning

confidence: 99%

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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Aryl and vinyl cyclopropanes through the in situ generation of B-cyclopropyl-9-BBN and its Suzuki–Miyaura coupling

Cited by 26 publications

References 21 publications

Stereospecific Couplings of Secondary and Tertiary Boronic Esters

Stereospecific Couplings of Secondary and Tertiary Boronic Esters

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

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

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