Copper‐Catalyzed Remote C(sp<sup>3</sup>)−H Trifluoromethylation of Carboxamides and Sulfonamides

Zhonglin Liu, Haiwen Xiao, Benxiang Zhang, Haigen Shen, Lin Zhu, Chaozhong Li

Angewandte Chemie International Edition · 2019 · 200 citations · 53 references

Concepts

Abstract

Abstract Reported herein is an unprecedented protocol for trifluoromethylation of unactivated aliphatic C(sp 3 )−H bonds. With Cu(OTf) 2 as the catalyst, the reaction of N‐fluoro‐substituted carboxamides (or sulfonamides) with Zn(CF 3 ) 2 complexes provides the corresponding δ‐trifluoromethylated carboxamides (or sulfonamides) in satisfactory yields under mild reaction conditions. A radical mechanism involving 1,5‐hydrogen atom transfer of N‐radicals followed by CF 3 ‐transfer from Cu II −CF 3 complexes to the thus formed alkyl radicals is proposed.

References

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