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

Haibo Mei; Jiang Liu; Romana Pajkert; Li Wang; Gerd-Volker Röschenthaler; Jianlin Han

doi:10.1039/D0QO01394C

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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†

Haibo Mei,

^a Jiang Liu,^a Romana Pajkert,^b Li Wang,^a Gerd-Volker Röschenthaler

*^b and Jianlin Han

*^a

Author affiliations

* Corresponding authors

^a Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
E-mail: hanjl@njfu.edu.cn

^b Department of Life Sciences and Chemistry, Jacobs University Bremen gGmbH, Campus Ring 1, 28759 Bremen, Germany
E-mail: G.Roeschenthaler@jacobs-university.de

Abstract

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.

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Article information

DOI: https://doi.org/10.1039/D0QO01394C
Article type: Research Article
Submitted: 08 Nov 2020
Accepted: 16 Dec 2020
First published: 04 Jan 2021

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Org. Chem. Front., 2021,8, 767-772

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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

H. Mei, J. Liu, R. Pajkert, L. Wang, G. Röschenthaler and J. Han, Org. Chem. Front., 2021, 8, 767 DOI: 10.1039/D0QO01394C

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Organic Chemistry Frontiers

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

Abstract

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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

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