Corey–Fuchs reaction

[4] The phosphine can be partially substituted by zinc dust, which can improve yields and simplify product separation.

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.

The second part of the reaction converts the isolable gem-dibromoalkene intermediate to the alkyne.

[3] The 50% H-incorporation could be explained by deprotonation of the (acidic) terminal deuterium with excess BuLi.