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

页码：7611 / 7615

页数：5

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