Journal
CHEM
Volume 7, Issue 7, Pages 1843-1851Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2021.03.010
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Funding
- National Natural Science Foundation of China [21573044, 21672039, 21871051, 21873019, 22071027]
- Shanghai Science and Technology Committee [19DZ2270100]
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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.
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.
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