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Sulfonamide-Directed Chemo- and Site-Selective Oxidative Halogenation/Amination Using Halogenating Reagents Generated in Situ from Cyclic Diacyl Peroxides

Denghu Chang, Rong Zhao, Congyin Wei, Yuan Yao, Yang Liu and Lei Shi*

*Shenzhen Graduate School, Harbin Institute of Technology, Shenzhen 518055, China, Email: lshihit.edu.cn

D. Chang, R. Zhao, C. Wei, Y. Yao, Y. Liu, L. Shi, J. Org. Chem., 2018, 83, 3305-3315.

DOI: 10.1021/acs.joc.8b00243 (free Supporting Information)


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Abstract

The combination of phthaloyl peroxide with commercially available halide salts provides an unique halogenating system for Hofmann-Löffler-Freytag-type reactions to produce N-chloroamides, δ-brominated products, and even biologically relevant pyrrolidines under mild conditions in good yields.

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Key Words

N-H Chlorination, Pyrrolidines, Phthaloyl peroxide, Photochemistry


ID: J42-Y2018