4.8 Article

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

Journal

ORGANIC LETTERS
Volume 24, Issue 11, Pages 2143-2148

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00425

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Funding

  1. National Natural Science Foundation of China [22161054, 81760624]

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This study reports the first example of using commercially available 2-bromo-3,3,3-trifluoropropene as a radical acceptor to synthesize secondary trifluoromethylated alkyl bromides. The practicality of this method was further demonstrated by diverse derivations and direct modification of biologically active molecules.
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.

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