Reaction of vinylbromides with alkynes using ppm amounts of Pd as catalyst

Reaction of vinylbromides with alkynes using ppm amounts of Pd as catalyst

Biajoli*, André F. P.; Monteiro, Adriano L.

Abstract:

The 1,3-enyne is an important core structure often found in many naturally occurring and biologically active compounds. In addition, 1,3-enynes are also very useful synthetic intermediates. The Pdcatalyzed Sonogashira reaction is one of the most powerful methods for the synthesis of such compounds. Pd complexes containing phosphine ligands associated with copper(I) iodide are the most widely used catalysts for this reaction. In the past several years, some protocols using copper catalysts have been developed. Recently, we have shown that a catalytic system based on CuI/1,10- phenanthroline efficiently promotes the coupling between phenols or pyrazole with (E)- bromostilbene. Here we present our first results about the coupling of vinyl bromides with alkynes.

The 1,3-enyne is an important core structure often found in many naturally occurring and biologically active compounds. In addition, 1,3-enynes are also very useful synthetic intermediates. The Pdcatalyzed Sonogashira reaction is one of the most powerful methods for the synthesis of such compounds. Pd complexes containing phosphine ligands associated with copper(I) iodide are the most widely used catalysts for this reaction. In the past several years, some protocols using copper catalysts have been developed. Recently, we have shown that a catalytic system based on CuI/1,10- phenanthroline efficiently promotes the coupling between phenols or pyrazole with (E)- bromostilbene. Here we present our first results about the coupling of vinyl bromides with alkynes.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013822174633

Referências bibliográficas

• [1] 1 See for example: Feuerstein, M.; Chahen, L.; Douce, H.; aMaurice
• [2] Santelli, M.; Tetrahedron. 2006, 62, 112.
• [3] 2 See for example: Saha, D; Chatterjee, T; Mukherjee, M; Ranu, B.C.; J.
• [4] Org. Chem. 2012, 77, 9379.
• [5] 3 Limberger,J.; Leal, B.C.; Back, D.F.; Dupont, J.; Monteiro, A.L.; Adv.
• [6] Synth. Catal. 2012, 354, 1429.

Como citar:

Biajoli*, André F. P.; Monteiro, Adriano L.; "Reaction of vinylbromides with alkynes using ppm amounts of Pd as catalyst", p-199-199. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013822174633