Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

Author:

Qu ChuanhuaORCID,Huang Run,Li Yong,Liu Tong,Chen Yuan,Song Guiting

Abstract

Chemoselective sulfonylation and isonitrilation reactions for the divergent synthesis of valuable diarylmethyl sulfones and isonitrile diarylmethanes starting from easy-to-synthesize para-quinone methides (p-QMs) and commercially abundant p-toluenesulfonylmethyl isocyanide (TosMIC) by using respectively zinc iodide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as catalysts were developed. The distinguishing feature of this method is that TosMIC plays a dual role from the same substrates in the reaction: as a sulfonyl source or as an isonitrile source. The synthetic utility of this protocol was also demonstrated in the synthesis of difluoroalkylated diarylmethane 5 and diarylmethane ketone derivatives 6 and 7, which are important core structures in natural products and medicines.

Funder

National Natural Science Foundation of China

Science and Technology Research Program of Chongqing Municipal Education Commission

the Scientific Research Fondation of the Chongqing University of Arts and Sciences

Chongqing Natural Science Foundation Postdoctoral Science Foundation Project

Publisher

Beilstein Institut

Subject

Organic Chemistry

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