Details

Autor(en) / Beteiligte

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

Titel

Copper‐Catalyzed Remote C(sp3)−H Trifluoromethylation of Carboxamides and Sulfonamides

Ist Teil von

• Angewandte Chemie International Edition, 2019-02, Vol.58 (8), p.2510-2513

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Reported herein is an unprecedented protocol for trifluoromethylation of unactivated aliphatic C(sp3)−H bonds. With Cu(OTf)2 as the catalyst, the reaction of N‐fluoro‐substituted carboxamides (or sulfonamides) with Zn(CF3)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 CF3‐transfer from CuII−CF3 complexes to the thus formed alkyl radicals is proposed. From a distance: Chemoselective trifluoromethylation of unactivated C(sp3)−H bonds distal to the functional group was achieved under mild, copper‐catalyzed conditions. A radical mechanism involving 1,5‐hydrogen atom transfer of N‐radicals followed by CF3‐transfer from CuII−CF3 complexes to the thus formed alkyl radicals is proposed.