Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-Containing S-Heterocycles

被引：26

作者：

He, Jun-Xiong ^{[1
,2
]}

Zhang, Zhi-Hao ^{[1
,2
]}

Mu, Bo-Shuai ^{[1
,2
]}

Cui, Xiao-Yuan ^{[1
,2
]}

Zhou, Jian ^{[1
,2
,3
]}

Yu, Jin-Sheng ^{[1
,2
,4
]}

机构：

[1] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Shanghai 200062, Peoples R China

[2] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

[3] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[4] Hainan Normal Univ, Key Lab Trop Med Resource Chem, Minist Educ, Haikou 571158, Hainan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 13期

基金：

中国国家自然科学基金;

关键词：

MUKAIYAMA-MANNICH REACTION; ENOL SILYL ETHERS; ORGANOFLUORINE-ORGANOSILICON CHEMISTRY; ONE-POT SYNTHESIS; ALDOL REACTION; BOND FORMATION; DIFLUOROENOXYSILANES ACCESS; TRIFLUOROMETHYL KETONES; ASSISTED SYNTHESIS; HIGHLY EFFICIENT;

D O I：

10.1021/acs.joc.1c00754

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented catalyst-free reaction of benzo[b]thiophene-2,3-diones with difluoroenoxysilanes has been developed using either MeOH or H2O as the solvent, which constitutes a facile and efficient protocol for the solvent-controlled divergent synthesis of five- and seven-membered S-heterocycles featuring a gem-difluoromethylene group. A gram-scale synthesis and the diversification of the product transformations to other difluorinated S-heterocycles further highlight its utility.

引用

页码：9206 / 9217

页数：12

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