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Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates

Zhi-Yun Liu and Silas P. Cook*

*Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States, Email: sicookindiana.edu

Z.-Y. Liu, S. P. Cook, Org. Lett., 2021, 23, 739-744.

DOI: 10.1021/acs.orglett.0c04039 (free Supporting Information)



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Abstract

A light-driven, copper-mediated trifluoromethylation of O-alkyl thiocarbonates offers broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), orthogonality and practicality. A radical organometallic mechanism is proposed.


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proposed mechanism



Key Words

Barton-McCombie Reaction, benzylic trifluoromethanes, trifluoromethyl alkanes, TTMSS, photochemistry


ID: J54-Y2021