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: sicook
indiana.edu
Z.-Y. Liu, S. P. Cook, Org. Lett., 2021, 23, 739-744.
DOI: 10.1021/acs.orglett.0c04039
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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
