Issue 6, 2011
From the journal:

Organic & Biomolecular Chemistry

Heck reaction of arenediazonium salts with N,N-diprotected allylamines. Synthesis of cinnamylamines and indoles†

Sandro Cacchi,*a   Giancarlo Fabrizi,a   Antonella Goggiamania  and  Alessio Sferrazzaa  

* Corresponding authors

a Dipartimento di Chimica e Tecnologie del Farmaco, La Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy
E-mail: sandro.cacchi@uniroma1.it
Fax: +39(06)4991-2780
Tel: +39(06)4991-2795

Abstract

Novel palladium-catalyzed reactions of arenediazonium tetrafluoroborates with N,N-diprotected allylamines are presented. The reaction of arenediazonium tetrafluoroborates with N,N-(Boc)2 allylamine allows for an easy approach to cinnamylamines whereas using 2-alkynyl-N-(allyl)trifluoroacetanilides and 2-iodo-N-(allyl)trifluoroacetanilide the reaction provides a useful tool for appending indole rings to aniline fragments.

Graphical abstract: Heck reaction of arenediazonium salts with N,N-diprotected allylamines. Synthesis of cinnamylamines and indoles

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Article information

DOI
https://doi.org/10.1039/C0OB01052A
Article type
Communication
Submitted
19 Nov 2010
Accepted
19 Jan 2011
First published
21 Jan 2011

Org. Biomol. Chem., 2011,9, 1727-1730

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Heck reaction of arenediazonium salts with N,N-diprotected allylamines. Synthesis of cinnamylamines and indoles

S. Cacchi, G. Fabrizi, A. Goggiamani and A. Sferrazza, Org. Biomol. Chem., 2011, 9, 1727 DOI: 10.1039/C0OB01052A

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