Tandem reaction of propargylic alcohol, sulfonamide, and N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide

Yuanxun Zhu; Guangwei Yin; Deng Hong; Ping Lu; Yanguang Wang

doi:10.1021/ol103074d

Tandem reaction of propargylic alcohol, sulfonamide, and N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide

Org Lett. 2011 Mar 4;13(5):1024-7. doi: 10.1021/ol103074d. Epub 2011 Jan 26.

Authors

Yuanxun Zhu¹, Guangwei Yin, Deng Hong, Ping Lu, Yanguang Wang

Affiliation

¹ Department of Chemistry, Zhejiang University, Hangzhou, P R China.

PMID: 21268594
DOI: 10.1021/ol103074d

Abstract

An efficient and straightforward strategy for the synthesis of N-(2-haloinden-1-yl)arenesulfonamides from propargylic alcohols and sulfonamides is described. Allenesulfonamide is postulated to be the key intermediate for this tandem transformation.

Publication types

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

MeSH terms

Alkynes / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Iodinated / chemical synthesis*
Hydrocarbons, Iodinated / chemistry
Indenes / chemical synthesis*
Indenes / chemistry
Molecular Structure
Propanols / chemistry*
Succinimides / chemistry*
Sulfonamides / chemical synthesis*
Sulfonamides / chemistry

Substances

Alkynes
Hydrocarbons, Iodinated
Indenes
N-(2-iodoinden-1-yl)arenesulfonamide
Propanols
Succinimides
Sulfonamides
N-iodosuccinimide
propargyl alcohol