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Synthesis of Secondary Trifluoromethylated Alkyl Bromides Using 2-Bromo-3,3,3-trifluoropropene as a Radical Acceptor

Peng Guo, Maoling Tao, Wenwen Xu, An‐Jun Wang, Weipiao Li, Qiuli Yao, Jie Tong, Chun‐Yang He

2022Organic Letters38 citationsDOI

Abstract

Herein, the first example using commercially available 2-bromo-3,3,3-trifluoropropene (BTP) as a radical acceptor has been reported. Taking advantage of this strategy, a wide range of secondary trifluoromethylated alkyl bromides were synthesized in good to excellent yields with broad functional group tolerance by using redox-active esters as a radical precursor. The practicality of this protocol was further demonstrated by diverse derivations and direct modification of biologically active molecules.

Topics & Concepts

ChemistryAlkylAcceptorFunctional groupCombinatorial chemistryOrganic chemistryMoleculePhysicsPolymerCondensed matter physicsFluorine in Organic ChemistryRadical Photochemical ReactionsInorganic Fluorides and Related Compounds