Methane activation by a borenium complex

The selective functionalization of methane under ambient conditions remains a formidable challenge for chemists. While most studies have focused on transition metal complexes, much less attention has been devoted to molecular complexes based on non-metal elements, despite them being more sustainable and less environmentally impactful. Here, we report that an N-heterocyclic carbene-stabilized borenium complex can activate methane under relatively mild conditions. The resulting methylborenium complex can readily transfer the methyl group to catecholborane (HBcat), which can lead to a synthetic cycle for the conversion of methane to MeBcat. Both experimental and theoretical mechanistic studies suggest that the C-H bonds ofmethane are activated via a s-bond metathesis pathway. Such direct aliphatic C-H borylation can be extended to other alkanes, such as ethane and octane. The formed alkylborenium complexes can react with terminal alkynes via 1,2-alkylboration to install both the alkyl and boryl functionalities onto organic scaffolds.

Automated summary

The selective functionalization of methane under relatively mild conditions is achieved in this study, with the activation of methane leading to the conversion of methane to MEBcat through a synthetic cycle. The study demonstrates the potential of using non-metal elements for sustainable and less environmentally impactful transformations.