Corey–Fuchs reaction

Corey–Fuchs reaction
Named after Elias James Corey
Philip L. Fuchs
Reaction type Substitution reaction
Identifiers
Organic Chemistry Portal corey-fuchs-reaction
RSC ontology ID RXNO:0000146

The Corey–Fuchs reaction, also known as the Ramirez–Corey–Fuchs reaction, is a series of chemical reactions designed to transform an aldehyde into an alkyne. The formation of the 1,1-dibromoolefins via phosphine-dibromomethylenes was originally discovered by Desai, McKelvie and Ramirez. The phosphine can be partially substituted by zinc dust, which can improve yields and simplify product separation. The second step of the reaction to convert dibromoolefins to alkynes is known as Fritsch–Buttenberg–Wiechell rearrangement. The overall combined transformation of an aldehyde to an alkyne by this method is named after its developers, American chemists Elias James Corey and Philip L. Fuchs.

By suitable choice of base, it is often possible to stop the reaction at the 1-bromoalkyne, a useful functional group for further transformation.