Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-ContainingS-Heterocycles

Jun Xiong He; Zhi Hao Zhang; Bo Shuai Mu; Xiao Yuan Cui; Jian Zhou; Jin Sheng Yu

doi:10.1021/acs.joc.1c00754

Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-ContainingS-Heterocycles

Jun Xiong He
, Zhi Hao Zhang
, Bo Shuai Mu
, Xiao Yuan Cui
, Jian Zhou
, Jin Sheng Yu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University
CAS - Shanghai Institute of Organic Chemistry
Hainan Normal University

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

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-memberedS-heterocycles featuring agem-difluoromethylene group. A gram-scale synthesis and the diversification of the product transformations to other difluorinatedS-heterocycles further highlight its utility.

Original language	English
Pages (from-to)	9206-9217
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	86
Issue number	13
DOIs	https://doi.org/10.1021/acs.joc.1c00754
State	Published - 2 Jul 2021

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title = "Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-ContainingS-Heterocycles",

abstract = "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-memberedS-heterocycles featuring agem-difluoromethylene group. A gram-scale synthesis and the diversification of the product transformations to other difluorinatedS-heterocycles further highlight its utility.",

author = "He, \{Jun Xiong\} and Zhang, \{Zhi Hao\} and Mu, \{Bo Shuai\} and Cui, \{Xiao Yuan\} and Jian Zhou and Yu, \{Jin Sheng\}",

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year = "2021",

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doi = "10.1021/acs.joc.1c00754",

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TY - JOUR

T1 - Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-ContainingS-Heterocycles

AU - He, Jun Xiong

AU - Zhang, Zhi Hao

AU - Mu, Bo Shuai

AU - Cui, Xiao Yuan

AU - Zhou, Jian

AU - Yu, Jin Sheng

PY - 2021/7/2

Y1 - 2021/7/2

N2 - 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-memberedS-heterocycles featuring agem-difluoromethylene group. A gram-scale synthesis and the diversification of the product transformations to other difluorinatedS-heterocycles further highlight its utility.

AB - 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-memberedS-heterocycles featuring agem-difluoromethylene group. A gram-scale synthesis and the diversification of the product transformations to other difluorinatedS-heterocycles further highlight its utility.

UR - https://www.scopus.com/pages/publications/85108591555

U2 - 10.1021/acs.joc.1c00754

DO - 10.1021/acs.joc.1c00754

M3 - 文章

AN - SCOPUS:85108591555

SN - 0022-3263

VL - 86

SP - 9206

EP - 9217

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-ContainingS-Heterocycles

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