Synthesis of di/trifluoromethyl cyclopropane-dicarbonitriles via [2+1] annulation of fluoro-based diazoethanes with (alkylidene)malononitriles

Cheng-Feng Gao; Yue-Ji Chen; Jing Nie; Fa-Guang Zhang; Chi Wai Cheung; Jun-An Ma

doi:10.1039/d3cc03897a

Synthesis of di/trifluoromethyl cyclopropane-dicarbonitriles via [2+1] annulation of fluoro-based diazoethanes with (alkylidene)malononitriles

Chem Commun (Camb). 2023 Sep 28;59(78):11664-11667. doi: 10.1039/d3cc03897a.

Authors

Cheng-Feng Gao¹, Yue-Ji Chen¹, Jing Nie¹, Fa-Guang Zhang¹, Chi Wai Cheung¹, Jun-An Ma^{1

2}

Affiliations

¹ Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Frontiers Science Center for Synthetic Biology (Ministry of Education), Tianjin University, Tianjin 300072, P. R. China. zhangfg1987@tju.edu.cn.
² Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, 350207, P. R. China.

PMID: 37695256
DOI: 10.1039/d3cc03897a

Abstract

Herein, we describe a [2+1] annulation reaction of di/trifluorodiazoethane with (alkylidene)malononitriles. This protocol offers a streamlined synthesis of a wide range of stereospecific and densely functionalized difluoromethyl and trifluoromethyl cyclopropane-1,1-dicarbonitriles. Further functional group interconversions or skeletal elaborations afford structurally distinct cyclopropyl variants.