Design of (β-diazo-α,α-difluoroethyl)phosphonates and their application as masked carbenes in visible light-promoted coupling reactions with sulfonic acids
Design of (β-diazo-α,α-difluoroethyl)phosphonates and their application as masked carbenes in visible light-promoted coupling reactions with sulfonic acids
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DOI：
10.1039/d0qo01394c
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发表时间：
2021-02-21
影响因子：
5.4
通讯作者：
Han, Jianlin
中科院分区：
文献类型：
--
作者：
Mei, Haibo;Liu, Jiang;Han, Jianlin
我们详细阐述了一种以（β-氨基-α,α-二氟乙基）膦酸酯作为前体生成（2-重氮-1,1-二氟乙基）膦酸酯的方法，及其在光化学条件下与磺酸偶联反应中作为掩蔽卡宾的应用。包括氨基膦酸酯和磺酸在内的各种偶联配偶体在此反应中具有良好的耐受性，能够以良好的产率提供未知的磺酸酯。这种新型重氮化合物的策略为功能化二氟亚甲基膦酸酯的构建和氟代重氮化合物的转化提供了宝贵的前景。
We elaborate a method for the generation of (2-diazo-1,1-difluoroethyl)phosphonates from (beta-amino-alpha,alpha-difluoroethyl)phosphonates as precursors and their application as masked carbenes in coupling reactions with sulfonic acids under photochemical conditions. Varieties of coupling partners including aminophosphonates and sulfonic acids are well tolerated in this reaction affording unknown sulfonate esters in good yields. The strategy of this new diazo compound provides a valuable vista for the construction of functionalized difluoromethylene phosphonates and transformations of fluoro diazo compounds.