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Copper-Catalyzed Remote C(sp3)-H Sulfoximination and Silylation of N-Fluorocarboxamides
Xuesong Wang1, Rundong Fan2,3, Yuanyuan Peng2,3
1Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-Machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Hainan Medical University, Haikou 571199, P. R. China.
Abstract:
Herein, we report a practical and efficient methodology for synthesizing highly valuable sulfoximine- and silicon-substituted carboxylamides from copper-catalyzed remote C(sp3)-H sulfoximination and silylation of N-fluorocarboxamides under ambient conditions. The copper-catalyzed reactions proceed to undergo sequential single-electron transfer (SET), 1,5-hydrogen atom transfer (1,5-HAT), and cross-coupling steps, thus generating new C-N and C-Si bonds. Significantly, this practical transformation occurs under mild conditions and exhibits a broad substrate scope and high regioselectivity.
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