Iodine-Mediated Copper-Catalyzed Efficient α-C(sp2)-Thiomethylation of α-Oxoketene Dithioacetals with Dimethyl Sulfoxide in One Pot

被引：33

作者：

Shukla, Gaurav ^{[1
]}

Srivastava, Abhijeet ^{[1
]}

Nagaraju, Anugula ^{[1
]}

Raghuvanshi, Keshav ^{[2
]}

Singh, Maya Shankar ^{[1
]}

机构：

[1] Banaras Hindu Univ, Fac Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India

[2] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 18期

关键词：

cascade reaction; 1,4-diazabicyclo[2.2.2]octane (DABCO); dimethyl sulfoxide (DMSO); iodination; thiomethylation; SOLVENT-FREE CONDITIONS; ARYL HALIDES; HETEROAROMATIC ANNULATION; METHYL SULFONES; FACILE ACCESS; S BOND; DMSO; HETEROCYCLES; OXIDATION; SULFIDES;

D O I：

10.1002/adsc.201500634

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The direct alpha-Csp(2)-H functionalization and thiomethylation of a-oxoketene dithioacetals (DTAs) has been accomplished with dimethyl sulfoxide (DMSO) in the presence of iodine and a copper(I) salt for the first time. A prerequisite is the in situ iodination of the alpha-Csp(2) atom of dithioacetals that could offer other reaction channels. The operationally simple one-pot protocol includes region-defined consecutive iodination and sulfenylation of the challenging alpha-Csp(2)-H bond of dithioacetals employing cheap and readily available reagents. DMSO here plays a dual role as thiomethyl source and solvent.

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页码：3969 / 3976

页数：8

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