期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 8, 页码 2448-2458出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo2000176
关键词
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资金
- Natural Science Foundation of China [20872129, 21072170]
- Department of Education of Zhejiang Province [Z200908265]
- Fundamental Rsearch Fund for the Central Universities [2010QNA3004]
An efficient synthesis of trisubstituted alkenes including 1,2-heterodisubstituted alkenes has been described. Reactions of thiols and amines with 1,1-dibromo-1-alkenes in the presence of TBAF center dot 3H(2)O afford (Z)-2-bromovinyl sulfides and (Z)-2-bromovinyl amines regio- and stereoselectively. The reaction proceeds under catalyst-free conditions with high efficiency. The coupling reactions of the obtained products bearing bromine atoms with phenylacetylene and phenylboronic acid gave trisubstituted alkenes in good to excellent yields. Cross-coupling with various N, O, S, and P nucleophiles selectively generated 1,2-N,O, 1,2-N,S, 1,2-S,P, 1,2-S,S, and 1,2-S,O heterodisubstituted alkenes.
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