Issue 8, 2008
From the journal:

Dalton Transactions

Rhodium catalysed dehydrogenative borylation of alkenes: Vinylboronates via C–H activation†

Ibraheem A. I. Mkhalid,a   R. Benjamin Coapes,a   S. Natasha Edes,a   David N. Coventry,a   Fabio E. S. Souza,b   Rhodri Ll. Thomas,a   Jonathan J. Hall,a   Si-Wei Bi,c   Zhenyang Lin*c  and  Todd B. Marder*a  

* Corresponding authors

a Department of Chemistry, Durham University, Durham, UK
E-mail: todd.marder@durham.ac.uk
Fax: +44 (0)191 384 4737
Tel: +44 (0)191 334 2037

b Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada

c Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
E-mail: chzlin@ust.hk

Abstract

We present herein a high yield, highly selective catalytic synthesis of vinylboronate esters (VBEs), including 1,1-disubstituted VBEs, from alkenes without significant hydrogenation or hydroboration, using the simple catalyst precursor, trans-[RhCl(CO)(PPh3)2] (1), and the diboron reagents B2pin2 (2a, pin = pinacolato = OCMe2CMe2O) or B2neop2 (2b, neop = neopentylglycolato = OCH2CMe2CH2O), or the monoboron reagent HBpin, all of which are commercially available. The reactions were conducted at 80 °C using conventional heating, or in a microwave reactor at 150 °C.

Graphical abstract: Rhodium catalysed dehydrogenative borylation of alkenes: Vinylboronates via C–H activation

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Article information

DOI
https://doi.org/10.1039/B715584K
Article type
Paper
Submitted
10 Oct 2007
Accepted
22 Nov 2007
First published
20 Dec 2007

Dalton Trans., 2008, 1055-1064

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Rhodium catalysed dehydrogenative borylation of alkenes: Vinylboronates via C–H activation

I. A. I. Mkhalid, R. B. Coapes, S. N. Edes, D. N. Coventry, F. E. S. Souza, R. Ll. Thomas, J. J. Hall, S. Bi, Z. Lin and T. B. Marder, Dalton Trans., 2008, 1055 DOI: 10.1039/B715584K

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