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Difluorocarbene Addition to Alkenes and Alkynes in Continuous Flow

Pauline Rullière, Patrick Cyr and André B. Charette*

*Université de Montréal, Centre in Green Chemistry and Catalysis, Department of Chemistry, Faculty of Arts and Science, P.O. Box 6128, Station Downtown, Québec, Canada H3C 3J7, Email: andre.charetteumontreal.ca

P. Rullière, P. Cyr, A. B. Charette, Org. Lett., 2016, 18, 1988-1991.

DOI: 10.1021/acs.orglett.6b00573 (free Supporting Information)


Abstract

The application of continuous flow technology enabled a controlled generation of difluorocarbene from TMSCF3 and a catalytic quantity of NaI. The in situ generated electrophilic carbene reacts smoothly with a broad range of alkenes and alkynes to provide the corresponding difluorocyclopropanes and difluorocyclopropenes within 10 min residence time at high reaction concentrations.

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Flow reactor setup



Key Words

cyclopropanes, cyclopropenes, fluoroalkanes, flow chemistry


ID: J54-Y2016