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 inOrganic letters Vol. 23; no. 3; pp. 1130 - 1134
Main Authors Mei, Haibo, Wang, Li, Pajkert, Romana, Wang, Qian, Xu, Jingcheng, Liu, Jiang, Röschenthaler, Gerd-Volker, Han, Jianlin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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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.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00150