期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 13, 页码 5504-5512出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00844
关键词
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资金
- Zhejiang Provincial Natural Science Foundation [LY13B020007]
- National Natural Science Foundation of China [21272178, 21372178, 21572163]
The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with alpha-bromocarbonyl compounds leading efficiently to a-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)(2)-catalyzed hydration of TosMIC to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of a Cs2CO3 additive.
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