Modular synthesis of sulfonyl benzoheteroles by silver-catalyzed heteroaromatization of propargylic alcohols with p-toluenesulfonylmethyl isocyanide (TosMIC): dual roles of TosMIC

Jianquan Liu; Zhenhua Liu; Peiqiu Liao; Xihe Bi

doi:10.1021/ol5031316

Modular synthesis of sulfonyl benzoheteroles by silver-catalyzed heteroaromatization of propargylic alcohols with p-toluenesulfonylmethyl isocyanide (TosMIC): dual roles of TosMIC

Org Lett. 2014 Dec 5;16(23):6204-7. doi: 10.1021/ol5031316. Epub 2014 Nov 17.

Authors

Jianquan Liu¹, Zhenhua Liu¹, Peiqiu Liao¹, Xihe Bi^{1

2}

Affiliations

¹ †Department of Chemistry, Northeast Normal University, Changchun 130024, China.
² ‡State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.

PMID: 25402338
DOI: 10.1021/ol5031316

Abstract

A new silver-catalyzed heteroaromatization of propargylic alcohols with p-toluenesulfonylmethyl isocyanide (TosMIC) has been developed that provides an efficient and modular approach to sulfonyl benzoheteroles. For the first time, TosMIC plays a dual role in one reaction: sulfonyl source and ligand. An unprecedented deoxysulfonylation/hydration/condensation reaction pathway is disclosed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Benzene Derivatives / chemical synthesis*
Benzene Derivatives / chemistry
Catalysis
Heterocyclic Compounds, 2-Ring / chemical synthesis*
Heterocyclic Compounds, 2-Ring / chemistry
Molecular Structure
Nitriles / chemistry*
Propanols / chemistry*
Silver / chemistry*
Sulfones / chemical synthesis*
Sulfones / chemistry

Substances

Alkynes
Benzene Derivatives
Heterocyclic Compounds, 2-Ring
Nitriles
Propanols
Sulfones
Silver
propargyl alcohol