A general approach to stereospecific Pd-catalyzed cross-coupling reactions of benzylic stereocenters

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发布日期 2023-11-24

DOI 10.1039/D3SC04519F

影响因子 9.825

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摘要

We have developed a general process for the formation of enantioenriched benzylic stereocenters via stereospecific Pd-catalyzed cross-coupling reactions of enantioenriched benzylic tricyclohexyltin nucleophiles. This process proceeds with excellent stereospecificity for a remarkably broad scope of electrophilic coupling partners including aryl and heteroaryl halides and triflates, acid chlorides, thioesters, chloroformates, and carbamoyl chlorides. Thus, enantioenriched 1,1-diarylalkanes as well as formal products of asymmetric enolate arylation are readily accessed using this approach. We additionally provide the first demonstration of a Sn-selective cross-coupling reaction using a vicinal alkylborylstannane nucleophile. In these reactions, the presence of cyclohexyl spectator ligands on tin is essential to ensure selective transfer of the secondary benzylic unit from tin to palladium.

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来源期刊

Chemical Science

CiteScore: 14.4

自引率: 3.9%

年发文量: 1413

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A general approach to stereospecific Pd-catalyzed cross-coupling reactions of benzylic stereocenters

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来源期刊

Chemical Science

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