Synthesis of α-Sulfonyl Ketones via I2/TBHP Promoted Radical Sulfonylation of Silyl Enol Ethers with Sulfohydrazides under Mild Conditions

被引：4

作者：

Tang, Yucai ^{[1
]}

Qu, Huang ^{[1
]}

Zhang, Wenxi ^{[1
]}

Wang, Feifei ^{[1
]}

Wang, Gang ^{[1
]}

机构：

[1] Hunan Univ Arts & Sci, Coll Chem & Mat Engn, Hunan Prov Cooperat Innovat Ctr Construct & Dev D, Changde 415000, Peoples R China

来源：

CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 2020年 / 41卷 / 01期

基金：

中国国家自然科学基金;

关键词：

alpha-Sulfonyl ketone; Silyl enol ether; Sulfonylhydrazide; Radical reaction; EFFICIENT SYNTHESIS; HYPERVALENT IODINE; BETA-KETOSULFONES; SULFONYLHYDRAZIDES; ACETATES; ACETYLENES; STRATEGY; OLEFINS; ALKYNES; WATER;

D O I：

10.7503/cjcu20190424

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A I-2/TBHP mediated reaction of readily prepared silyl enol ethers with sulfonylhydrazides was developed for the synthesis of alpha-sulfonyl ketones under mild conditions. Twenty-two alpha-sulfonyl ketone derivatives were obtained in 22%-72% yields under the optimized reaction conditions. Their structures were confirmed by nuclear magnetic resonance spectroscopy (NMR). Moreover, the present catalytic protocol exhibited good functional group tolerance and substrate applicability, and various substituents such as halogen, nitro, trifluoromethyl, furan and naphthalene can be successfully converted to corresponding alpha-sulfonyl ketones. The preliminary mechanistic studies disclose that the reaction may proceed via a radical pathway.

引用

页码：118 / 124

页数：7

共 27 条

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