The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow

Beilstein J Org Chem. 2013 Sep 2:9:1781-90. doi: 10.3762/bjoc.9.207. eCollection 2013.

Abstract

The application of a monolithic form of triphenylphosphine to the Ramirez gem-dibromoolefination reaction using flow chemistry techniques is reported. A variety of gem-dibromides were synthesised in high purity and excellent yield following only removal of solvent and no further off-line purification. It is also possible to perform the Appel reaction using the same monolith and the relationship between the mechanisms of the two reactions is discussed.

Keywords: Ramirez gem-dibromoolefination reaction; bromination; flow chemistry; solid-supported reagent; triphenylphosphine monolith.