Carbon dioxide's low cost and renewability makes it an attractive C1 feedstock for construction of complex molecules.  However, the activation of CO2 is challenging due to its thermodynamic stability.  Recently, transition metal catalysis has emerged as a major strategy towards CO2 carboxylations at aryl and alkenyl positions.  However, few reports have described these transformations at sp3-type positions.  We report a transition metal-free CO2 carboxylation that displays excellent regioselectivity and surprising functional group tolerance. Alkyl carboxylic acid derivatives can be readily accessed from styrenes through a facile tandem process that eliminates the use of harsh, reactive organometallic reagents.   The methodology allows for the rapid installation of CO2 at a chiral center.  The scope of this hydrocarboxylation methodology has been explored, in addition to transformations that utilize electrophiles besides CO2.

Hydrocarboxylation of styrenes via transition metal-free CO<sub>2</sub> carboxylation

243rd National Meeting (2012)

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Hydrocarboxylation of styrenes via transition metal-free CO2 carboxylation

Hydrocarboxylation of styrenes via transition metal-free CO₂ carboxylation