Chromium-Catalyzed Defluorinative Reductive Coupling of Aldehydes with gem-Difluoroalkenes

Abstract

Herein, a mild and convenient defluorinative reductive cross coupling of gem-difluoroalkenes with aliphatic aldehydes has been developed to afford diverse silyl-protected β-fluorinated allylic alcohols. The reaction is operationally simple and shows good functional group tolerance with moderate to excellent yields. The utility of this method is demonstrated by converting the products into various bioactive fluorinated compounds, showing its potential applications in drug discovery and biochemistry.

Electrocatalysis-Enabled Defluorinative Cross-Coupling of gem-Difluoroalkenes with Aldehydes and Ketones

“…In this method, excessive manganese reductant and chlorotrimethylsilane (TMSCl) were indispensable, but despite that, the reaction was ineffective for ketones (Scheme 1c). 13 Electrochemical synthesis has proven to be a robust and environmentally friendly approach for redox organic transformations. Electroreduction takes electrons as green reducing agents, which avoids the use of expensive chemicals as reductants and enables the reaction to be performed under mild conditions.…”

“…Recently, Yu and Pan reported a chromium-catalyzed cross-coupling reaction of gem -difluoroalkenes with aldehydes. In this method, excessive manganese reductant and chlorotrimethylsilane (TMSCl) were indispensable, but despite that, the reaction was ineffective for ketones (Scheme c) . Electrochemical synthesis has proven to be a robust and environmentally friendly approach for redox organic transformations.…”