Issue 33, 2015
From the journal:

Chemical Communications

Thiophene synthesis via 1,1-carboboration†

Christina Eller,ab   Gerald Kehr,a   Constantin G. Daniliuc,‡a   Douglas W. Stephan*b  and  Gerhard Erker*a  

* Corresponding authors

a Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, 48149 Münster, Germany
E-mail: erker@uni-muenster.de
Fax: +49-251-8336503

b Department of Chemistry University of Toronto, 80 St. George Street, Toronto, ON, Canada

Abstract

Reaction of bis(tert-butylethynyl)sulfide with the boron Lewis acid reagents X–B(C6F5)2 (X = CH3, Cl, C6F5) in pentane at r.t. gave the respective borylated thiophenes in a sequence of 1,1-carboboration reactions. In contrast, bis(phenylethynyl)sulfide reacted with B(C6F5)3 only in a 2 : 1 molar ratio to give a benzothiophene derivative.

Graphical abstract: Thiophene synthesis via 1,1-carboboration

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Article information

DOI
https://doi.org/10.1039/C5CC01806D
Article type
Communication
Submitted
05 Mar 2015
Accepted
19 Mar 2015
First published
20 Mar 2015

Chem. Commun., 2015,51, 7226-7229

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Thiophene synthesis via 1,1-carboboration

C. Eller, G. Kehr, C. G. Daniliuc, D. W. Stephan and G. Erker, Chem. Commun., 2015, 51, 7226 DOI: 10.1039/C5CC01806D

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