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. 2020 Feb 17;59(8):3053-3057.
doi: 10.1002/anie.201912739. Epub 2020 Jan 21.

Synthesis of Chiral Triarylmethanes Bearing All-Carbon Quaternary Stereocenters: Catalytic Asymmetric Oxidative Cross-Coupling of 2,2-Diarylacetonitriles and (Hetero)arenes

Zehua Wang  1 , Yasheng Zhu  2 , Xiaoguang Pan  2 , Gang Wang  1 , Lei Liu  1   2
Affiliations

Synthesis of Chiral Triarylmethanes Bearing All-Carbon Quaternary Stereocenters: Catalytic Asymmetric Oxidative Cross-Coupling of 2,2-Diarylacetonitriles and (Hetero)arenes

Zehua Wang et al. Angew Chem Int Ed Engl. .

Abstract

A direct and enantioselective oxidative cross-coupling of racemic 2,2-diarylacetonitriles with electron-rich (hetero)arenes has been described, which allows for efficient construction of triarylmethanes bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivity. The reaction has an excellent functional group tolerance, and exhibits a broad scope with respect to both 2,2-diarylacetonitrile and (hetero)arene components. The rich chemistry of the cyano group allows for facile synthesis of other valuable chiral triarylmethanes bearing all-carbon quaternary centers that are otherwise difficult to access.

Keywords: asymmetric catalysis; nitrile; oxidative C−H functionalization; quaternary stereocenter; triarylmethane.

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