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. 2022 Jul 6;144(26):11546-11552.
doi: 10.1021/jacs.2c04037. Epub 2022 Jun 23.

Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters

Ningxin Xu  1 , Hao Liang  1 , James P Morken  1
Affiliations

Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters

Ningxin Xu et al. J Am Chem Soc. .

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1.
Scheme 1.
Activation and Coupling of Alkylboronic Esters with Cu-based Catalysts.
Scheme 2.
Scheme 2.
Application of Cu-Catalyzed Coupling to a Galbulin Derivative (a) and Gram-Scale Coupling (b)
See this image and copyright information in PMC

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