A one-pot metal-free protocol for the synthesis of chalcogenated furans from 1,4-enediones and thiols

被引：19

作者：

Rajeshkumar, Venkatachalam ^{[1
]}

Neelamegam, Chinnaraj ^{[1
]}

Anandan, Sambandam ^{[1
]}

机构：

[1] Natl Inst Technol, Dept Chem, Tiruchirappalli 620015, Tamil Nadu, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 04期

关键词：

SULFA-MICHAEL ADDITION; C-H CHALCOGENATION; REGIOSELECTIVE SULFENYLATION; SINGLET-OXYGEN; IODINE; ALPHA; FUNCTIONALIZATION; HETEROCYCLES; THIOLATION; ALKYNES;

D O I：

10.1039/c8ob03051k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transition-metal-free synthesis of chalcogenated furans through the sequential thiol-Michael/Paal-Knorr reaction of 1,4-enediones in the presence of a catalytic amount of p-toluenesulfonic acid has been developed. The present one-pot strategy involves the thiol Michael addition to 1,4-enediones in an anti-Markovnikov fashion with the formation of a new C-S bond, followed by intramolecular dehydrative annulation in the presence of cat. TsOH delivering fully substituted furans in good to excellent yields (50-99%). The reaction is compatible with a wide range of substrates and also capable of multi-gram scale synthesis of chalcogenated furans.

引用

页码：982 / 991

页数：10

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