Metal-Free, Radical Addition to Alkenes via Desulfitative Chlorine Atom Transfer

被引：19

作者：

Cao, Lidong ^{[1
]}

Weidner, Karin ^{[1
]}

Renaud, Philippe ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 18期

基金：

瑞士国家科学基金会;

关键词：

amides; atom-transfer radical addition (ATRA) reaction; chlorine atom transfer; desulfitation; esters; radical reaction; sulfonyl chloride; trichloromethyl radical; TRANSFER CYCLIZATION REACTIONS; ALPHA-IODO ESTERS; RUTHENIUM(II) COMPLEX; COORDINATION SPHERE; ASYMMETRIC ADDITION; SULFONYL CHLORIDE; KHARASCH REACTION; ALKYL RADICALS; ATRC REACTIONS; RATE CONSTANTS;

D O I：

10.1002/adsc.201100473

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient method for radical additions to unactivated alkenes via desulfitative chlorine-atom transfer is described. The reaction is based on the use of readily available sulfonyl chlorides as starting materials and cheap radical initiators such as azobisisobutyronitrile (AIBN), di-tert-butyldiazene (DTBD), and dilauroyl peroxide (DLP). No transition metal catalyst is required and the reaction takes place under mild conditions at temperatures <= 85 degrees C.

引用

页码：3467 / 3472

页数：6

共 50 条

[31] Conventional Type II photoinitiators as activators for photoinduced metal-free atom transfer radical polymerization
Allushi, Andrit
Kutahya, Ceren
Aydogan, Cansu
Kreutzer, Johannes
Yilmaz, Gorkem
Yagci, Yusuf
POLYMER CHEMISTRY, 2017, 8 (12) : 1972 - 1977
[32] Computational studies of copper-catalyzed and photoinduced metal-free atom transfer radical polymerization
Fang, Cheng
Pan, Xiangcheng
Fantin, Marco
Gennaro, Armando
Matyjaszewski, Krzysztof
Liu, Peng
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[33] Oxygen-tolerant photo-induced metal-free atom transfer radical polymerization
Xu, Xinmeng
Xu, Xiang
Zeng, Yanning
Zhang, Faai
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2021, 411
[34] Photoinduced Metal-Free Atom Transfer Radical Polymerization Using Highly Conjugated Thienothiophene Derivatives
Kutahya, Ceren
Allushi, Andrit
Isci, Recep
Kreutzer, Johannes
Ozturk, Turan
Yilmaz, Gorkem
Yagci, Yusuf
MACROMOLECULES, 2017, 50 (17) : 6903 - 6910
[35] Metal-Free Atom Transfer Radical Polymerization of Methyl Methacrylate with ppm Level of Organic Photocatalyst
Huang, Zhicheng
Gu, Yu
Liu, Xiaodong
Zhang, Lifen
Cheng, Zhenping
Zhu, Xiulin
MACROMOLECULAR RAPID COMMUNICATIONS, 2017, 38 (10)
[36] Recyclable Bio-Based Photoredox Catalyst in Metal-Free Atom Transfer Radical Polymerization
Wang, Yanan
Li, Huili
Dong, Jinhuan
Hu, Lijun
Wei, Donglei
Bai, Liangjiu
Yang, Huawei
Chen, Hou
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2021, 222 (07)
[37] Cu-Catalyzed atom transfer radical addition reactions of alkenes with α-bromoacetonitrile
Pu, Weiya
Sun, Dani
Fan, Wanyue
Pan, Wenwen
Chai, Qinghui
Wang, Xiaoxing
Lv, Yunhe
CHEMICAL COMMUNICATIONS, 2019, 55 (33) : 4821 - 4824
[38] Metal-free, intermolecular carbopyridylation of alkenes via visible-light-induced reductive radical coupling
Chen, Dan
Xu, Lei
Long, Tianyu
Zhu, Shengqing
Yang, Jun
Chu, Lingling
CHEMICAL SCIENCE, 2018, 9 (48) : 9012 - 9017
[39] Metal-free photoinduced electron transfer-atom transfer radical polymerization (PET-ATRP) via a visible light organic photocatalyst
Liu, Xiaodong
Zhang, Lifen
Cheng, Zhenping
Zhu, Xiulin
POLYMER CHEMISTRY, 2016, 7 (03) : 689 - 700
[40] Frustrated-radical-pair-initiated atom transfer radical addition of perfluoroalkyl halides to alkenes
Xie, Fuyu
He, Jianghua
Zhang, Yuetao
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (15) : 3861 - 3869

← 1 2 3 4 5 →