Issue 13, 2012
From the journal:

Chemical Communications

1,1-Carboboration

Gerald Kehr*a  and  Gerhard Erker*a  

* Corresponding authors

a Organisch-Chemisches Institut der Universität Münster, Corrensstr. 40, 48149 Münster, Germany
E-mail: erker@uni-muenster.de, kehrald@uni-muenster.de

Abstract

The use of very electrophilic boranes RB(C6F5)2 widens the scope of the 1,1-carboboration reaction substantially. Simple terminal alkynes HC[triple bond, length as m-dash]CR undergo this reaction with the RB(C6F5)2 reagents rapidly under mild conditions to give high yields of very useful new alkenylborane products. Even internal alkynes RC[triple bond, length as m-dash]CR undergo 1,1-carboboration with the RB(C6F5)2 reagents to provide a novel way of carbon–carbon σ-bond activation. Variants of these reactions involving phosphorus substituted alkynes and more complex bisalkynyl main group and transition metal substrates give rise to the formation of very interesting functionalized metallacyclic products upon treatment with RB(C6F5)2 reagents by means of reaction sequences involving selective 1,1-carboboration steps.

Graphical abstract: 1,1-Carboboration

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Article information

DOI
https://doi.org/10.1039/C1CC15628D
Article type
Feature Article
Submitted
12 Sep 2011
Accepted
24 Oct 2011
First published
24 Nov 2011

Chem. Commun., 2012,48, 1839-1850

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1,1-Carboboration

G. Kehr and G. Erker, Chem. Commun., 2012, 48, 1839 DOI: 10.1039/C1CC15628D

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