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Issue 6, 2011
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Heck reaction of arenediazonium salts with N,N-diprotected allylamines. Synthesis of cinnamylamines and indoles

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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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Publication details

The article was received on 19 Nov 2010, accepted on 19 Jan 2011 and first published on 21 Jan 2011


Article type: Communication
DOI: 10.1039/C0OB01052A
Citation: 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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