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Synthesis of internal alkynes via one-pot palladium-catalyzed and dehydrobromination reactions of 1,1-dibromo-1-alkenes

Chelucci, Giorgio Adolfo and Capitta, Francesca and Baldino, Salvatore (2008) Synthesis of internal alkynes via one-pot palladium-catalyzed and dehydrobromination reactions of 1,1-dibromo-1-alkenes. Tetrahedron, Vol. 64 (44), p. 10250-10257. ISSN 0040-4020. Article.

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DOI: 10.1016/j.tet.2008.08.020

Abstract

Tandem palladium-catalyzed cross-coupling of alkyl, alkenyl, alkynyl, aryl, and heteroaryl 2-substituted 1,1-dibromo-1-alkenes with aryl or heteroaryl boronic acids or borate esters and dehydrobromination of the intermediate coupled products afforded internal alkynes in moderate to good yields (up to 89%). The synthesis has been carried out in a one-pot process and in a two-step sequence according to the nature of the starting 1,1-dibromoalkenes. The reported protocol is compatible with the presence in the 1,1-dibromo-1-alkene molecule of additional reactive halogen–carbon bonds, thus allowing to build up more complex alkyne derivatives.

Item Type:Article
ID Code:1358
Status:Published
Refereed:Yes
Uncontrolled Keywords:Alkynes, alkenes, 1,1-dibromoalkenes, Suzuki–Miyaura reaction, palladium catalysts
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Pergamon / Elsevier
ISSN:0040-4020
Copyright Holders:© 2008 Elsevier
Deposited On:18 Aug 2009 10:04

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