A convenient synthesis of amides and nitriles with a branched and conjugated dienyne structure

Babudri, Francesco; Fiandanese, V; Marchese, G; Punzi, Angela

doi:10.1016/S0040-4020(02)01282-6

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An efficient and stereoselective synthetic approach to a variety of amides and nitriles with a branched and conjugated dienyne structure has been developed, starting from a readily available mono-silylated unsaturated amide and nitrile with an enyne structure. A nucleophilic hydrohalogenation of the triple bond of the enynes with NaI afforded a Z,E-iododienamide and a Z,E-iododienenitrile that, subjected to palladium-catalyzed cross-coupling reactions with a variety of terminal alkynes, led directly to the title compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

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Titolo:	A convenient synthesis of amides and nitriles with a branched and conjugated dienyne structure
Autori:	BABUDRI, Francesco FIANDANESE V MARCHESE G PUNZI, Angela mostra contributor esterni nascondi contributor esterni
Data di pubblicazione:	2002
Rivista:	TETRAHEDRON
Citazione:	A convenient synthesis of amides and nitriles with a branched and conjugated dienyne structure / BABUDRI F; FIANDANESE V; MARCHESE G; PUNZI A. - In: TETRAHEDRON. - ISSN 0040-4020. - 58:47(2002), pp. 9547-9552.
Abstract:	An efficient and stereoselective synthetic approach to a variety of amides and nitriles with a branched and conjugated dienyne structure has been developed, starting from a readily available mono-silylated unsaturated amide and nitrile with an enyne structure. A nucleophilic hydrohalogenation of the triple bond of the enynes with NaI afforded a Z,E-iododienamide and a Z,E-iododienenitrile that, subjected to palladium-catalyzed cross-coupling reactions with a variety of terminal alkynes, led directly to the title compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.
Handle:	http://hdl.handle.net/11586/125616
Appare nelle tipologie:	1.1 Articolo in rivista

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