Iron-Catalyzed Cyclopropanation with Trifluoroethylamine Hydrochloride and 
Olefins in Aqueous Media: In Situ Generation of Trifluoromethyl Diazomethane

Morandi, Bill; Carreira, Erick M.

doi:10.1002/anie.200905573

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Iron-Catalyzed Cyclopropanation with Trifluoroethylamine Hydrochloride and Olefins in Aqueous Media: In Situ Generation of Trifluoromethyl Diazomethane

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Morandi, Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Laboratorium für Organische Chemie, ETH Zürich, 8093 Zürich (Switzerland) ;

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Morandi, B., & Carreira, E. M. (2010). Iron-Catalyzed Cyclopropanation with Trifluoroethylamine Hydrochloride and Olefins in Aqueous Media: In Situ Generation of Trifluoromethyl Diazomethane. Angewandte Chemie International Edition, 49(5), 938-941. doi:10.1002/anie.200905573.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0026-A1C2-1

Abstract

Let's avoid the risk! The title transformation has been developed for the synthesis of trifluoromethyl-substituted cyclopropane derivatives (see scheme). It avoids the preparation of trifluoromethyl diazomethane and merges a number of areas: water as a reaction medium, iron catalysis, and access to reactive intermediates under operationally safe conditions.