Design of (β-diazo-α,α-difluoroethyl)phosphonates and their application as masked carbenes in visible light-promoted coupling reactions with sulfonic acids,Organic Chemistry Frontiers

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Design of (β-diazo-α,α-difluoroethyl)phosphonates and their application as masked carbenes in visible light-promoted coupling reactions with sulfonic acids
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-1-4 , DOI: 10.1039/d0qo01394c
Haibo Mei _{1,

2,

3,

4,

5} , Jiang Liu _{1,

2,

3,

4,

5} , Romana Pajkert _{6,

7,

8,

9} , Li Wang _{1,

2,

3,

4,

5} , Gerd-Volker Röschenthaler _{6,

7,

8,

9} , Jianlin Han _{1,

2,

3,

4,

5}

Affiliation

We elaborate a method for the generation of (2-diazo-1,1-difluoroethyl)phosphonates from (β-amino-α,α-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.

中文翻译：

（β-重氮-α，α-二氟乙基）膦酸酯的设计及其在可见光促进的与磺酸偶联反应中作为掩蔽的卡宾的应用

我们阐述了一种由（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的卡宾的应用。。在该反应中，包括氨基膦酸酯和磺酸在内的各种偶联伴侣均被很好地耐受，从而以高收率提供了未知的磺酸酯。这种新的重氮化合物的策略为官能化的二氟亚甲基膦酸酯的构建和氟重氮化合物的转化提供了宝贵的前景。

更新日期：2021-01-04

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