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Remote Directed Isocyanation of Unactivated C(sp3)–H Bonds: Forging Seven-Membered Cyclic Ureas Enabled by Copper Catalysis

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journal contribution
posted on 24.01.2020, 17:42 by Hongwei Zhang, Peiyuan Tian, Lishuang Ma, Yulu Zhou, Cuiyu Jiang, Xufeng Lin, Xiao Xiao
Reported herein is an unprecedented copper-catalyzed site-selective δ-C­(sp3)–H bonds activation of aliphatic sulfonamides for constructing the synthetically useful seven-membered N-heterocycles. A key to success is the use of in-situ-formed amide radicals, to activate the inert C­(sp3)–H bond, and inexpensive TMSNCO, as a coupling reagent under mild conditions. To the best of our knowledge, this represents the first use of alkylamine derivatives as a five-membered synthon to prepare a seven-membered N-heterocycles.