Ligated boryl radicals (LBRs), generated from Lewis base-coordinated boranes, have emerged as powerful tools capable of halogen-atom transfer (XAT) processes. Nevertheless, metal-free LBR-enabled radical chemistry remains largely confined to radical additions or cascade pathways. Herein, we report a green-light-induced cyclopropanation of alkenes using dichloromethane (DCM) as a C1 synthon, enabled by the synergistic action of N-heterocyclic nitrenium (NHN) catalysts and LBRs. This work demonstrates a transition-metal-free cyclopropanation of alkenes with DCM, further highlighting the synthetic potential of the NHN/LBR cooperative strategy.
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Chang-Zhen Fang
University of Chinese Academy of Sciences
Hui Liu
Beijing Institute of Technology
Zi-Hao Xia
Chinese Academy of Sciences
Organic Letters
University of Chinese Academy of Sciences
Ministry of Agriculture and Rural Affairs
Shandong University of Technology
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Fang et al. (Fri,) studied this question.
synapsesocial.com/papers/6975b2c8feba4585c2d6e4ee — DOI: https://doi.org/10.1021/acs.orglett.6c00039