Anionic Triflyldiazomethane: Generation and Its Application for Synthesis of Pyrazole-3-triflones via [3+2] Cycloaddition Reaction

作者：Das, Pulakesh; Gondo, Satoshi; Tokunaga, Etsuko; Sumii, Yuji; Shibata, Norio^*

来源：Organic Letters, 2018, 20(3): 558-561.

DOI：10.1021/acs.orglett.7b03664

• BIOLOGICAL-ACTIVITY
• TRIFLUOROMETHYLTHIOLATION REACTIONS
• REGIOSELECTIVE SYNTHESIS
• ENANTIOSELECTIVE FLUORINATION
• STEREOSELECTIVE-SYNTHESIS
• DIAZOCARBONYL COMPOUNDS
• ASYMMETRIC-SYNTHESIS
• HAMMETT CONSTANTS
• VINYL TRIFLONES
• DIFLUOROMETHYLTHIOLATION

The synthesis of pyrazole triflones containing a triflyl group at the 3-position is disclosed. Treatment of 2-diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one with nitroalkenes under basic conditions gave pharmaceutically attractive pyrazole 3-triflones in good to high yields. The generation of anionic triflyldiazomethane species followed by the [3 + 2] cycloaddition reaction with nitroalkenes is proposed for this transformation. 3-(Difluoromethanesulfonyl)pyrazoles were also synthesized by using a previously unknown anionic (difluoromethanesulfonyl)diazomethane species under a similar strategy.

• 出版日期2018-2-2
• 单位浙江师范大学