Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters

Chem Sci. 2022 Mar 15;13(15):4327-4333. doi: 10.1039/d2sc00968d. eCollection 2022 Apr 13.

Abstract

Herein we describe the first construction of fluorinated tertiary stereocenters based on an alkene C(sp2)-C(sp2) bond cleavage. The new process, that takes advantage of a Rh-catalyzed carbyne transfer, relies on a branched-selective fluorination of tertiary allyl cations and is distinguished by a wide scope including natural products and drug molecule derivatives as well as adaptability to radiofluorination.