Insights into the Factors Controlling the Origin of Activation Barriers in Group 13 Analogues of the Four-Membered N-Heterocyclic Carbenes.

ABSTRACT: The mechanisms of C-H bond insertion and alkene cycloaddition were investigated theoretically using five model systems: group 13 analogues of the four-membered nucleophilic N-heterocyclic carbenes (NHCs) (1E; E = group 13 element). The theoretical findings indicate that, except for 1B with H₂C=CH₂, these four-membered NHCs undergo insertion and [1 + 2] cycloaddition reactions with difficulty because their activation barriers are quite high (31 kcal/mol). The theoretically confirmed chemical inertness of the four-membered NHCs 1Ga and 1In might explain why they have been experimentally detected at room temperature. Additionally, our theoretical observations indicate that the reactivity of these four-membered NHCs featuring a central g

SUBMITTER: Zhang ZF 

PROVIDER: S-EPMC8412915 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature