Metal-catalyzed direct carboxylation of unactivated alkyl halides with CO2

Metal-catalyzed direct carboxylation of unactivated alkyl halides with CO2

Liu, Yu; Martin, Ruben

Abstract:

The exploitation of carbon dioxide as a C1 source has attracted much attention due to the fact that it is a renewable, inexpensive, nontoxic and environment-friendly carbon feedstock. In recent years, the catalytic carboxylation of arylmetal species, alkynes and activated C-H bonds has been well documented in the literature. We2a and others2b have also developed the carboxylation of aryl halides with CO2 leading to benzoic acids. Recently, we described the first catalytic carboxylation of primary, secondary and tertiary benzyl halides with CO2 en route to phenylacetic acids (Figure 1). Despite the advances realized, to the best of our knowledge the direct carboxylation of unactivated alkyl halides with CO2 has not been reported.

The exploitation of carbon dioxide as a C1 source has attracted much attention due to the fact that it is a renewable, inexpensive, nontoxic and environment-friendly carbon feedstock. In recent years, the catalytic carboxylation of arylmetal species, alkynes and activated C-H bonds has been well documented in the literature. We2a and others2b have also developed the carboxylation of aryl halides with CO2 leading to benzoic acids. Recently, we described the first catalytic carboxylation of primary, secondary and tertiary benzyl halides with CO2 en route to phenylacetic acids (Figure 1). Despite the advances realized, to the best of our knowledge the direct carboxylation of unactivated alkyl halides with CO2 has not been reported.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201362534256

Referências bibliográficas

• [1] 1 For selected reviews, see: (a) Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kühn, F. E. Angew. Chem. Int. Ed. 2011, 50, 8510. (b) Correa, A.; Martin, R. Angew. Chem. Int. Ed. 2009, 48, 6201. (c) Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
• [2] 2 (a) Correa, A.; Martin, R. J. Am. Chem. Soc. 2009, 131, 15974. (b) Fujihara, T.; Nogi, K.; Xu, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2012, 134, 9106.
• [3] 3 Leon, T.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1221.
• [4] 4 For selected reviews on the activation of alkyl halides, see: (a) Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656. (b) Frish, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674.

Como citar:

Liu, Yu; Martin, Ruben; "Metal-catalyzed direct carboxylation of unactivated alkyl halides with CO2", p-35-35. 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_201362534256