Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates

被引：18

作者：

Mulina, Olga M. ^{[1
]}

Ilovaisky, Alexey I. ^{[1
,2
]}

Opatz, Till ^{[3
]}

Terent'ev, Alexander O. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Zelinsky Inst Organ Chem, 47 Leninsky Prospect, Moscow 119991, Russia

[2] All Russian Res Inst Phytopathol, B Vyazyomy 143050, Moscow Region, Russia

[3] Johannes Gutenberg Univ Mainz, Dept Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

来源：

TETRAHEDRON LETTERS | 2021年 / 64卷

基金：

俄罗斯科学基金会;

关键词：

Photoredox catalysis; Oxidation; Sulfonylation; Vinyl azides; Sulfinates; EFFICIENT APPROACH; EOSIN Y; ALKENES; SULFONES; SULFONYLATION; KI;

D O I：

10.1016/j.tetlet.2020.152737

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：4

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