Electron Donor–Acceptor Complex Enabled Radical Cyclization of α-Diazodifluoroethyl Sulfonium Salt with Unactivated Alkynes,Organic Letters

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Electron Donor–Acceptor Complex Enabled Radical Cyclization of α-Diazodifluoroethyl Sulfonium Salt with Unactivated Alkynes
Organic Letters ( IF 4.9 ) Pub Date : 2023-12-13 , DOI: 10.1021/acs.orglett.3c03790
Ming-Yue He ₁ , Xiaodong Tang _{1,

2} , Hao-Yan Wu ₁ , Jing Nie ₁ , Jun-An Ma _{1,

2} , Fa-Guang Zhang ₁

Affiliation

An α-diazodifluoroethane sulfonium reagent was developed in this study to undergo [3 + 2] radical cyclization with unactivated alkynes to give the corresponding 3-difluoromethyl pyrazoles under blue light irradiation conditions. The key to the success of this transformation lies in the formation of an electron donor–acceptor (EDA) complex between an electron-deficient α-diazo sulfonium salt and an electron-rich triaryl amine. This study circumvents a major substrate scope limitation in polar cycloaddition reactions of existent diazodifluoroethane reagents.

中文翻译：

电子供体-受体配合物使α-重氮二氟乙基锍盐与未活化的炔发生自由基环化

本研究开发了一种α-重氮二氟乙锍试剂，在蓝光照射条件下与未活化的炔烃进行[3+2]自由基环化，得到相应的3-二氟甲基吡唑。这种转化成功的关键在于缺电子的α-重氮锍盐和富电子的三芳胺之间形成电子供体-受体（EDA）络合物。这项研究规避了现有重氮二氟乙烷试剂极性环加成反应中主要底物范围的限制。

更新日期：2023-12-13

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