1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO₂CH₂F): a versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via Julia–Kocienski olefination

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• 作者：Lingui Zhu ; Chuanfa Ni ; Yanchuan Zhao ; Jinbo Hu
• 关键词：Fluoromethyl sulfone ; Monofluroalkene ; Julia– ; Kocienski olefination ; Fluoroolefination
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：3 July 2010
• 年：2010
• 卷：66
• 期：27-28
• 页码：5089-5100
• 全文大小：1652 K

文摘

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 α-alkylated, acylated, and phenylsulfonylated to give corresponding α-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via Julia–Kocienski olefination reactions.