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In this comment, insights gained from density functional the- ory into the mechanism by which the Cu(I)-catalyzed boracar- boxylation of vinyl arenes occurs with specific focus on the CO2 insertion step are presented. Preliminary calculations indicated a potential non-covalent interaction between boron and CO2 in the carboxylation transition state, implicating cooperative CO2 activation. A study of boron Lewis acidity was conducted through substitution of sp2 mono-boron substituents. An inverse correlation between boron valence deficiency (BVD) and the enthalpic barrier of CO2 insertion into the β- borylbenzyl-Cu(I) bond was revealed, supporting Lewis acid/ base cooperativity between boron and the proximal oxygen of CO2 at the carboxylation insertion transition state. These find- ings suggest that future methodology development should consider strategic incorporation of similar Lewis acidic func- tionality to facilitate carboxylation of challenging substrates.