Efficient 1,4-addition of alpha-substituted fluoro(phenylsulfonyl)methane derivatives to alpha,beta-unsaturated compounds

The 1,4-addition of a monofluoromethyl nucleophile to a variety of alpha,beta-unsaturated compounds has been achieved under mild conditions using either phosphines or potassium carbonate at room temperature. alpha-Substituted fluoro(phenylsulfonyl)methane easily undergoes Michael addition to alpha,b...

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Published in:Beilstein journal of organic chemistry 2008-05, Vol.4 (1), p.17
Main Authors: Prakash, G K Surya, Zhao, Xiaoming, Chacko, Sujith, Wang, Fang, Vaghoo, Habiba, Olah, George A
Format: Article
Language:English
Subjects:
Chemistry
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Summary:The 1,4-addition of a monofluoromethyl nucleophile to a variety of alpha,beta-unsaturated compounds has been achieved under mild conditions using either phosphines or potassium carbonate at room temperature. alpha-Substituted fluoro(phenylsulfonyl)methane easily undergoes Michael addition to alpha,beta-unsaturated ketones, esters, nitriles, sulfones, as well as propynoates at room temperature to yield the corresponding adducts in moderate to excellent yields.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.4.17