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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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
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container_issue 3
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container_title Organic letters
container_volume 23
creator Mei, Haibo
Wang, Li
Pajkert, Romana
Wang, Qian
Xu, Jingcheng
Liu, Jiang
Röschenthaler, Gerd-Volker
Han, Jianlin
description 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.
doi_str_mv 10.1021/acs.orglett.1c00150
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title In Situ Generation of Unstable Difluoromethylphosphonate-Containing Diazoalkanes and Their Use in [3 + 2] Cycloaddition Reactions with Vinyl Sulfones
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