In Situ Generation of Unstable Difluoromethylphosphonate-Containing Diazoalkanes and Their Use in [3 + 2] Cycloaddition Reactions with Vinyl Sulfones

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 diazoalk...

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Bibliographic Details
Published in:Organic letters 2021-02, Vol.23 (3), p.1130-1134
Main Authors: Mei, Haibo, Wang, Li, Pajkert, Romana, Wang, Qian, Xu, Jingcheng, Liu, Jiang, Röschenthaler, Gerd-Volker, Han, Jianlin
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00150