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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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.
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