Tandem C-C/C-N Bond Formation via Rh(III)-Catalyzed α-Fluoroalkenylation and Sequential Annulation of 2-Arylquinazolinones and -Difluorostyrenes.

J Org Chem

Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.

Published: January 2023

An efficient method of Rh(III)-catalyzed coupling reaction between 2-arylquinazolinones and -difluorostyrenes has been developed. In this work, two diverse structures of monofluoroalkenes and isoindolo[1,2-]quinazolin-10(12)-one derivatives were respectively synthesized by controlling the amount of additives (Ca(OH) and AgNTf) to achieve controlled stepwise breaking of the C-F bonds of -difluorostyrenes. This reaction has the characteristics of a wide range of substrates and good functional group tolerance. Meanwhile, several control experiments were conducted and a plausible mechanism was proposed.

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http://dx.doi.org/10.1021/acs.joc.2c02006DOI Listing

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