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; Lei Shi

doi:10.1021/acs.joc.8b00243

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
, Lei Shi^*

^*Corresponding author for this work

Harbin Institute of Technology Shenzhen
School of Chemistry and Chemical Engineering, Harbin Institute of Technology
Nankai University

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

The combination of cyclic diacyl peroxides with commercially available halide salts as a unique halogenating system is utilized in Hofmann-Löffler-Freytag-type reaction. This strategy allows for the formation of N-chloroamides, δ-brominated products, and even biologically relevant pyrrolidines under mild conditions in moderate to excellent yields. Meanwhile, the preliminary structure of the in situ formed brominating reagent is investigated by NMR and UV/vis analysis.

Original language	English
Pages (from-to)	3305-3315
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	83
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.8b00243
State	Published - 16 Mar 2018
Externally published	Yes

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

abstract = "The combination of cyclic diacyl peroxides with commercially available halide salts as a unique halogenating system is utilized in Hofmann-L{\"o}ffler-Freytag-type reaction. This strategy allows for the formation of N-chloroamides, δ-brominated products, and even biologically relevant pyrrolidines under mild conditions in moderate to excellent yields. Meanwhile, the preliminary structure of the in situ formed brominating reagent is investigated by NMR and UV/vis analysis.",

author = "Denghu Chang and Rong Zhao and Congyin Wei and Yuan Yao and Yang Liu and Lei Shi",

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T1 - Sulfonamide-Directed Chemo- and Site-Selective Oxidative Halogenation/Amination Using Halogenating Reagents Generated in Situ from Cyclic Diacyl Peroxides

AU - Chang, Denghu

AU - Zhao, Rong

AU - Wei, Congyin

AU - Yao, Yuan

AU - Liu, Yang

AU - Shi, Lei

PY - 2018/3/16

Y1 - 2018/3/16

N2 - The combination of cyclic diacyl peroxides with commercially available halide salts as a unique halogenating system is utilized in Hofmann-Löffler-Freytag-type reaction. This strategy allows for the formation of N-chloroamides, δ-brominated products, and even biologically relevant pyrrolidines under mild conditions in moderate to excellent yields. Meanwhile, the preliminary structure of the in situ formed brominating reagent is investigated by NMR and UV/vis analysis.

AB - The combination of cyclic diacyl peroxides with commercially available halide salts as a unique halogenating system is utilized in Hofmann-Löffler-Freytag-type reaction. This strategy allows for the formation of N-chloroamides, δ-brominated products, and even biologically relevant pyrrolidines under mild conditions in moderate to excellent yields. Meanwhile, the preliminary structure of the in situ formed brominating reagent is investigated by NMR and UV/vis analysis.

UR - https://www.scopus.com/pages/publications/85044167990

U2 - 10.1021/acs.joc.8b00243

DO - 10.1021/acs.joc.8b00243

M3 - 文章

C2 - 29484885

AN - SCOPUS:85044167990

SN - 0022-3263

VL - 83

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

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

Abstract

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