Copper‐Catalyzed Arylation of Remote C(sp3)−H Bonds in Carboxamides and Sulfonamides |
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| Authors: | Dr. Zhaodong Li Dr. Qian Wang Prof. Dr. Jieping Zhu |
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| Affiliation: | 1. http://lspn.epfl.ch;2. Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, Lausanne, Switzerland |
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| Abstract: | Reported herein is an unprecedented copper‐catalyzed arylation of remote C(sp3)?H bonds. Stirring a trifluorotoluene solution of either N‐fluorocarboxamides or N‐fluorosulfonamides and arylboronic acids in the presence of a catalytic amount of copper(II) trifluoroacetylacetonate, 2,2′‐bipyridine, and sodium tert‐butoxide afforded the γ‐ and δ‐C(sp3)?H arylated carboxamides and sulfonamides, respectively, in good to high yields. Mechanistic studies indicate that the reaction might proceed through an amidyl radical generation, 1,5‐hydrogen atom transfer (HAT), and copper‐catalyzed cross‐coupling of the resulting carbon radical with arylboronic acids. |
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| Keywords: | C− H functionalization copper cross-coupling homogeneous catalyst radicals |
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