1,4-Diazabicyclo[2.2.2]octane-Promoted Aminotrifluoromethylthiolation of α,β-Unsaturated Carbonyl Compounds: N-Trifluoromethylthio-4-nitrophthalimide Acts as Both the Nitrogen and SCF3 Sources

• DOI: 10.1021/acs.orglett.5b03116
• Publication Date: 2015-12-10T14:57:08Z
• Authors: Qing Xiao; Qijie He; Juncheng Li; Jun Wang
• Keywords: DABCO; Nitrogen atom; Reaction conditions

A novel difunctionalization reaction is described. It uses N-trifluoromethylthio-4-nitrophthalimide as the reagent, which serves both nitrogen and SCF3 sources. In presence of DABCO (1,4-diazabicyclo[2.2.2]octane), groups can be incorporated into α,β-unsaturated carbonyl compounds easily give versatile β-amino ketones esters in good yields. This features mild conditions, high atom-economy, efficient access to α-SCF3 amino acids.