In Situ Generation of Unstable Difluoromethylphosphonate-Containing Diazoalkanes and Their Use in [3 + 2] Cycloaddition Reactions with Vinyl Sulfones
Haibo Mei, Li Wang, Romana Pajkert, Qian Wang, Jingcheng Xu, Jiang Liu, Gerd‐Volker Röschenthaler, Jianlin Han
Abstract
A [3 + 2] cycloaddition reaction of unstable difluoromethylphosphonate-containing diazoalkanes with vinyl sulfones under simple reaction conditions is developed, which provides an efficient route toward functionalized fluorinated pyrazolines derivatives in good chemical yields. The difluoro diazoalkanes are generated in situ using t-BuONO for the diazotization of (β-amino-α,α-difluoroethyl)phosphonates, and their stabilities and reactivities were carefully investigated.
Topics & Concepts
ChemistryCycloadditionIn situReaction conditionsOrganic chemistryCombinatorial chemistryCatalysisFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions