期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 27, 页码 8414-8422出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200939
关键词
alkynylation; anti-Michael reactions; density functional calculations; organolithiums; sulfonylacetylenes
资金
- Spanish Government [CTQ-2009-12168, CTQ2010-17006]
- CAM [AVANCAT CS2009/PPQ-1634]
- Consejo Nacional de Ciencia y Tecnologia de Mexico
- Ministerio de Educacion y Ciencia
We describe the unexpected behavior of the arylsulfonylacetylenes, which suffer an anti-Michael addition of organolithiums producing their alkynylation under very mild conditions. The broad scope, excellent yields, and simplicity of the experimental procedure are the main features of this methodology. A rational explanation of all these results can be achieved by theoretical calculations, which suggest that the association of the organolithiums to the electrophile is a previous step of their intramolecular attack and is responsible for the unexpected anti-Michael reactions observed for substituted sulfonylacetylenes.
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