Terminal Trifluoromethylation of Ketones via Selective C-C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents
Shuang Wu, Junzhao Li, Ru He, Kunfang Jia and Yiyun Chen*
*Shanghai Institute of Organic Chemistry, University of
Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road,
Shanghai 200032, China, Email: yiyunchen
sioc.ac.cn
S. Wu, J. Li, R. He, K. Jia, Y. Chen, Org. Lett., 2021, 23, 9204-9209.
DOI: 10.1021/acs.orglett.1c03526
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Abstract
A selective C-C bond cleavage of cycloalkanols enables the synthesis of aryl and alkyl ketones trifluoromethylated at the γ, δ, ε, position or more remote terminal sites. This reaction was scalable to gram-scale, applicable to structurally complex steroid trifluoromethylation, and extendable to pentafluoroethylation.
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proposed mechanism
Key Words
trifluoromethylation, photochemistry
ID: J54-Y2021
