Issue 20, 2005
From the journal:

Organic & Biomolecular Chemistry

Palladium catalysed aryl amination reactions in supercritical carbon dioxide

Catherine J. Smith,*a   Melanie W. S. Tsang,abc   Andrew B. Holmes,*bc   Rick L. Danheiserd  and  Jefferson W. Testerd  

* Corresponding authors

a Melville Laboratory, Department of Chemistry, Lensfield Road, Cambridge, UK

b School of Chemistry, University of Melbourne, Vic. 3010, Australia

c Bio21 Institute, University of Melbourne, 30 Flemington Road, Parkville, Vic. 3010, Australia
E-mail: aholmes@unimelb.edu.au
Fax: +613 83442384
Tel: +613 83442344

d Departments of Chemistry and Chemical Engineering, Massachusetts Institute of Technology, Cambridge, MA 02139-4307, USA

Abstract

Palladium catalysed C–N bond formation in supercritical carbon dioxide has been accomplished. Carbamic acid formation is avoided in part through the use of an N-silylamine as the coupling partner. Employing a catalyst system of Pd2dba3 (1 mol%) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (2 mol%) enabled the catalytic amination of aryl bromides and chlorides with N-silylanilines to be realised in excellent yield. Extension of the methodology to the N-arylation of N-silyldiarylamines, N-silylazoles and N-silylsulfonamides is reported.

Graphical abstract: Palladium catalysed aryl amination reactions in supercritical carbon dioxide

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B509345G
Article type
Paper
Submitted
04 Jul 2005
Accepted
29 Jul 2005
First published
13 Sep 2005

Org. Biomol. Chem., 2005,3, 3767-3781

Permissions

Request permissions

Palladium catalysed aryl amination reactions in supercritical carbon dioxide

C. J. Smith, M. W. S. Tsang, A. B. Holmes, R. L. Danheiser and J. W. Tester, Org. Biomol. Chem., 2005, 3, 3767 DOI: 10.1039/B509345G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements