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Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters.

ABSTRACT: Copper-catalyzed stereospecific cross-couplings of boronic esters are reported. Boron "ate" complexes derived from pinacol boronic esters and tert-butyl lithium undergo stereospecific transmetalation to copper cyanide, followed by coupling with alkynyl bromides, allyl halides, propargylic halides, β-haloenones, hydroxylamine esters, and acyl chlorides. Through this simple transformation, commercially available inexpensive compounds can be employed to convert primary and secondary alkylboronic esters to a wide array of synthetically useful compounds.

SUBMITTER: Xu N

PROVIDER: S-EPMC10436227 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters.

Xu Ningxin N Liang Hao H Morken James P JP

Journal of the American Chemical Society 20220623 26

Copper-catalyzed stereospecific cross-couplings of boronic esters are reported. Boron "ate" complexes derived from pinacol boronic esters and <i>tert</i>-butyl lithium undergo stereospecific transmetalation to copper cyanide, followed by coupling with alkynyl bromides, allyl halides, propargylic halides, β-haloenones, hydroxylamine esters, and acyl chlorides. Through this simple transformation, commercially available inexpensive compounds can be employed to convert primary and secondary alkylbor ...[more]

PMID: 35735669

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