Issue 61, 2014
From the journal:

Chemical Communications

Face to face activation of a phenylselenium borane with α,β-unsaturated carbonyl substrates: facile synthesis of C–Se bonds†

Xavier Sanz,ab   Christopher M. Vogels,c   Andreas Decken,d   Carles Bo,*b   Stephen A. Westcott*c  and  Elena Fernández*a  

* Corresponding authors

a Department Química Física i Inorgànica, University Rovira i Virgili, C/Marcel·li Domingo, s/n, Tarragona, Spain
E-mail: mariaelena.fernandez@urv.cat

b Institute of Chemical Research of Catalonia (ICIQ), Avda. Països Catalans, 16, 43007 Tarragona, Spain
E-mail: cbo@iciq.cat

c Department of Chemistry and Biochemistry, Mount Allison University, Sackville, NB, Canada
E-mail: swestcott@mta.ca

d Department of Chemistry, University of New Brunswick, Fredericton, NB, Canada

Abstract

Activated olefins directly react with a phenylselenium borane, at room temperature, without any metal or organocatalytic assistance. Up to 10 examples of β-(phenylseleno) substituted ketones and aldehydes have been prepared and theoretical evidence for the mechanism opens up non-existing pathways to create C–heteroatom bonds as a general tool.

Graphical abstract: Face to face activation of a phenylselenium borane with α,β-unsaturated carbonyl substrates: facile synthesis of C–Se bonds

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Article information

DOI
https://doi.org/10.1039/C4CC02098G
Article type
Communication
Submitted
20 Mar 2014
Accepted
03 Jun 2014
First published
11 Jun 2014

Chem. Commun., 2014,50, 8420-8423

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Face to face activation of a phenylselenium borane with α,β-unsaturated carbonyl substrates: facile synthesis of C–Se bonds

X. Sanz, C. M. Vogels, A. Decken, C. Bo, S. A. Westcott and E. Fernández, Chem. Commun., 2014, 50, 8420 DOI: 10.1039/C4CC02098G

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