1034144-31-4Relevant articles and documents
1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): A versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via JuliaKocienski olefination
Zhu, Lingui,Ni, Chuanfa,Zhao, Yanchuan,Ru, Jinbo
supporting information; experimental part, p. 5089 - 5100 (2010/08/20)
1-tert-Butyl-IH-tetrazol-5-yl fluoromethyl sulfone (TBTSO 2CI-12F) has been developed as a new and efficient fluoromethylidene synthon for the synthesis of both terminal and internal monofluoroalkenes via JuliaKocienski olefination reaction. The base-mediated reaction between TBTSO2CI-12F 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. TBTSO 2CI-12F reagent was also found to be readily CL-alkylated, acylated, and phenylsulfonylated to give corresponding CL-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via JuliaKocienski olefination reactions.