期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 28, 页码 10484-10491出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja403627k
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资金
- U.S. National Science Foundation
- French Agence Nationale de Recherche [ANR-11-BS07-008]
- UHA
- ENSCMu
- CNRS
- Actelion
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1265652] Funding Source: National Science Foundation
Reactions of 1,3-dimethylimidazol-2-ylidene-borane (diMe-Imd-BH3) and related NHC-boranes with diaryl and diheteroaryl disulfides provide diverse NHC-boryl monosulfides (diMe-Imd-BH2SAr) and NHC-boryl disulfides (diMe-Imd-BH(SAr)(2)). Heating in the dark with 1 equiv of disulfide favors monosulfide formation, while irradiation with 2 equiv disulfide favors disulfide formation. With heteroaryl disulfides, the NHC-borane in the primary NHC-boryl sulfide product migrates from sulfur to nitrogen to give new products with a thioamide substructure. Most substitution reactions are thought to proceed through radical chains in which homolytic substitution of a disulfide by an NHC-boryl radical is a key step. However, with electrophilic disulfides under dark conditions, a competing ionic path may also be possible.
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