Highly selective synthesis of 6-substituted benzothiophenes by Sc(OTf)3-catalyzed intermolecular cyclization and sulfur migration-Reference-Cited by-同舟云学术

Highly selective synthesis of 6-substituted benzothiophenes by Sc(OTf)3-catalyzed intermolecular cyclization and sulfur migration

Published:2016 Issue:12 Volume:3 Page:1619-1623
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Wang Xiaoming¹²³⁴,Gensch Tobias¹²³⁴,Glorius Frank¹²³⁴

Affiliation:

1. Westfälische Wilhelms- Universität Münster

2. Organisch-Chemisches Institut

3. 48149 Münster

4. Germany

Abstract

A series of 6-substituted benzo[b]thiophenes was synthesized using a Sc(OTf)₃-catalyzed intermolecular cyclization between para-substituted N-(arylthio)succinimides and alkynes taking advantage of a unique and selective 1,2-sulfur migration occuring via an electrophilic ipso cyclization to a key spirocyclic thiete intermediate.

Funder

European Research Council

Alexander von Humboldt-Stiftung

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2016/QO/C6QO00477F

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