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Ruben Martin

Ruben Martin

Seminar
Tue, Sep. 6, 2016, 4:30pm - 6:00pm
Frick Chemistry Laboratory, Taylor Auditorium
Host: Robert Knowles

Ni-catalyzed Reductive Carboxylation Techniques and C-O Cleavage

Activation of inert entities has been and continues to be of extreme interest to any organic chemist.1 This is especially true with activation of atmospheric molecules such as CO22 or the activation of relatively inert C-O bonds.3 The development of operationally-simple and practical catalytic methods for the activation of the above-mentioned entities would be highly desirable, as many of the current methods involve the use of stoichiometric amounts or air-sensitive organometallic reagents. In the last years, our research group has reported some progress directed towards the functionalization of C-O bonds and catalytic reductive carboxylation of organic matter with CO2 (Scheme 1).4 These methods are characterized by their simplicity, wide substrate scope, including challenging substrate combinations with particularly sensitive functional groups and a diverse set of substitution patterns.
 
 
Scheme 1. Metal-catalyzed reductive carboxylation events and C-O bond-cleavage
(1) Activation of Unreactive Bonds in Organic Synthesis, Springer, Berlin 1999
(2) Tsuji, Y.; Fujihara, T. Chem. Commun. 2012, 48, 9956.
(3) Cornella, J.; Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43, 8081.
(4) Selected recent examples: (a) Correa. A.; Leon, T.; Martin, R. J. Am. Chem. Soc. 2014, 136, 1062. (b) Zarate, C.; Martin, R. J. Am. Chem. Soc. 2014, 136, 2236. (c) Liu, Y.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 11212. (d) Moragas, T.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 17702. (e) Zarate, C.; Manzano, R.; Martin, R. J. Am. Chem. Soc. 2015, 137, 6754. (f) Wang, X.; Liu,Y.; Martin, R. J. Am. Chem. Soc. 2015, 137, 6476.