期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 22, 页码 10664-10671出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01549
关键词
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资金
- National Natural Science Foundation of China [21302048]
- Hunan Provincial Natural Science Foundation of China [14JJ7028, 2016JJ4035]
- Scientific Research Hunan Provincial Education Department [15B095]
- Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province [2012-318]
- Construct Program of Key Discipline in Hunan Province
We report the atom-economic and environmentally friendly synthesis of Z-beta-sulfonyl-a,beta-unsaturated carbonyl compounds in water. The mechanism study reveals that the hydrosulfonylation of alkynylcarbonyl compounds with sulfinic acids proceeds via a mechanism that features a sulfinic acid molecule protonating an alkynyl motif to form the ethenium intermediate, which subsequently reacted with a sulfonyl anion to afford the desired products. The ethenium intermediate differentiated electronic and steric demands between the two substituents on the C C triple bond of the alkyne substrates to exhibit high regio- and stereoselectivity from a wide range of Z-beta-sulfonyl-a,beta-unsaturated carbonyl compounds.
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