Visible-Light-Enabled Oxidative Alkylation of Unactivated Alkenes with Dimethyl Sulfoxide through Concomitant 1,2-Aryl Migration

被引：57
|
作者：
Lu, Maojian [1 ]
Qin, Honggui [1 ]
Lin, Zhaowei [1 ]
Huang, Mingqiang [1 ]
Weng, Wen [1 ]
Cai, Shunyou [1 ,2 ]
机构：
[1] Minnan Normal Univ, Sch Chem Chem Engn & Environm, Key Lab Modern Analyt Sci & Separat Technol Fujia, Zhangzhou 363000, Peoples R China
[2] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Key Lab Chem Genom, Shenzhen 518055, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 23期
基金：
中国国家自然科学基金;
关键词：
HYDROGEN-ATOM TRANSFER; C-H BONDS; CENTERED RADICALS; PUMMERER REACTION; ALLYLIC ALCOHOLS; GENERATION; NICKEL; FORMYLATION; EFFICIENT; CHEMISTRY;
D O I：
10.1021/acs.orglett.8b03340
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Metal-free oxidative radical 1,2-alkylarylation of unactivated alkenes with the alpha-C(sp(3))-H bond of dimethyl sulfoxide has been developed. This study realizes a new, conceptually novel technology for convenient construction of a variety of alpha-aryl-gamma-methylsulfinyl ketones in good-to-excellent yields with the synergistic interactions of visible light irradiation, organic fluorophores 4CzIPN, and hypervalent iodine(III) reagent under transition-metal free conditions. A remarkable kinetic isotope effect was observed, which helped provide insight into the reaction's mechanistic course.
引用
收藏
页码：7611 / 7615
页数：5
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