Iron-Catalyzed Allylic Defluorinative Ketone Olefin Coupling

In this protocol, we demonstrate our discovery that iron is able to efficiently catalyze the reductive allylic defluorinative ketyl olefin coupling reaction between alpha-trifluoromethyl alkenes and unactivated ketones. This operationally simple cross-electrophile reaction circumvents the use of pre-generated organometallics and allows for the synthesis of diverse functional-group-rich tertiary gem-difluorohomoallylic alcohols through a polarity-reversed strategy. Preliminary mechanistic studies support a mechanism that proceeds through a ketyl formation/olefin insertion/beta-fluoro elimination sequence.

Automated summary

Iron is shown to efficiently catalyze a reaction between alpha-trifluoromethyl alkenes and unactivated ketones, resulting in the synthesis of diverse functional-group-rich compounds. This operation is simple and does not require pre-generated organometallics.