Palladium Catalyzed Heck Oxyarylation in Lawsone Derivatives

Palladium Catalyzed Heck Oxyarylation in Lawsone Derivatives

Frota, Lívia C. R. M. da; Ramalho, Larissa B.; Silva, Alcides J. M. da; Costa, Paulo R. R.

Abstract:

Palladium catalyzed oxyarrylation of chromens, firstly reported by Horino and cols, is a powerful tool to synthesize isoflavonoids. Catalytic versions for this reaction were reported by Larock and Kiss. Mechanistic studies on the oxyarylation of olefins by ortho-iodophenols in the presence of silver carbonate as base, as well as the use of microwave irradiation, were recently described by our group. In this work we compared the Heck oxyarylation reaction of Lawsone (1a) and 3-iododerivative (1b) with olefin 2 under different conditions (Scheme 1, Table 1).

Palladium catalyzed oxyarrylation of chromens, firstly reported by Horino and cols, is a powerful tool to synthesize isoflavonoids. Catalytic versions for this reaction were reported by Larock and Kiss. Mechanistic studies on the oxyarylation of olefins by ortho-iodophenols in the presence of silver carbonate as base, as well as the use of microwave irradiation, were recently described by our group. In this work we compared the Heck oxyarylation reaction of Lawsone (1a) and 3-iododerivative (1b) with olefin 2 under different conditions (Scheme 1, Table 1).

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DOI: 10.5151/chempro-14bmos-R0035-1

Referências bibliográficas

• [1] 1Horino, H.; Inoue, N. Bull. Soc. Jpn. 1971, 44, 3210.
• [2] 2Costa, P.R.R. and cols Bioorg. Med. Chem. 2006, 14, 7962 and cited references.
• [3] 3 Emrich, D. E.; Larock, R. C. J. Organomet. Chem. 2004, 689, 3756.
• [4] 4 Kiss, L.; Antus, S.; Heterocycl. Commun. 2000, 6, 309.
• [5] 5 Costa, P. R. R. J. Organomet. Chem. 2010, 695, 2062.
• [6] 6Costa, P.R.R. and cols Eur. J. Org. Chem., 2011 in press.
• [7] 7Le Bras, J; Muzart, J. chem. Rev., 2011, 111, 1170.

Como citar:

Frota, Lívia C. R. M. da; Ramalho, Larissa B.; Silva, Alcides J. M. da; Costa, Paulo R. R.; "Palladium Catalyzed Heck Oxyarylation in Lawsone Derivatives", p-35-35. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0035-1