Copper Catalyzed C-O and C-N Coupling of Vinyl Bromides with Phenols and Azoles

Copper Catalyzed C-O and C-N Coupling of Vinyl Bromides with Phenols and Azoles

Limberger, Jones; Monteiro, Adriano Lisboa

Abstract:

In the past years significant improvements were achieved for the copper-catalyzed C-O and C-N coupling reactions. The use of appropriate ligands allowed the efficiently coupling reaction under mild conditions and low catalyst loadings. Therefore, important building blocks of organic synthesis can be selectively produced. In this context vinylethers and vinylamines can be easily obtained through the coupling of phenols/azoles with vinyl halides. In present work, we performed the coupling of substituted phenols and azoles with (E)- bromostilbene and bromotriphenylethene using a simple catalytic system composed by CuI and phenantroline. By using this protocol we were able to produce tri- and tetra-substituted vinylethers and vinylamines in good to excellent yields (Scheme 1).

In the past years significant improvements were achieved for the copper-catalyzed C-O and C-N coupling reactions. The use of appropriate ligands allowed the efficiently coupling reaction under mild conditions and low catalyst loadings. Therefore, important building blocks of organic synthesis can be selectively produced. In this context vinylethers and vinylamines can be easily obtained through the coupling of phenols/azoles with vinyl halides. In present work, we performed the coupling of substituted phenols and azoles with (E)- bromostilbene and bromotriphenylethene using a simple catalytic system composed by CuI and phenantroline. By using this protocol we were able to produce tri- and tetra-substituted vinylethers and vinylamines in good to excellent yields (Scheme 1).

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DOI: 10.5151/chempro-14bmos-R0149-1

Referências bibliográficas

• [1] 1 Monnier, F.; Taillefer, M. Angew. Chem. Int. Ed. 2009, 48, 6954.
• [2] 2 Taillefer, M.; Ouali, A.; Renard, B.; Spindler, J. F. Chem. Eur. J. 2006, 12, 5301.

Como citar:

Limberger, Jones; Monteiro, Adriano Lisboa; "Copper Catalyzed C-O and C-N Coupling of Vinyl Bromides with Phenols and Azoles", p-149-149. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0149-1