Journal
TETRAHEDRON
Volume 66, Issue 27-28, Pages 5089-5100Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.04.113
Keywords
Fluoromethyl sulfone; Monofluroalkene; Julia-Kocienski olefination; Fluoroolefination
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Funding
- National Natural Science Foundation of China [20772144, 20825209, 20832008]
- Chinese Academy of Sciences
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1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F) has been developed as a new and efficient fluoromethylidene synthon for the synthesis of both terminal and internal monofluoroalkenes via Julia-Kocienski olefination reaction. The base-mediated reaction between TBTSO2CH2F and carbonyl compounds (aldehydes and ketones) provided terminal monofluoroalkenes in good yields with moderate E/Z selectivity. The dominance of E- or Z-fluoroalkenes could be controlled by selection of proper reaction solvent and temperature. TBTSO2CH2F reagent was also found to be readily a-alkylated, acylated, and phenylsulfonylated to give corresponding alpha-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via Julia-Kocienski olefination reactions. (C) 2010 Elsevier Ltd. All rights reserved.
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