Issue 6, 2011

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

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

Supplementary files

Article information

Article type
Communication
Submitted
19 Nov 2010
Accepted
19 Jan 2011
First published
21 Jan 2011

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

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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