Triphenylphosphine-assisted dehydroxylative Csp3–N bond formation via electrochemical oxidation

Zhimin Xu; Yue Zheng; Zhihui Wang; Xiaoqing Shao; Lifang Tian; Yahui Wang

doi:10.1039/C9CC08622F

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Triphenylphosphine-assisted dehydroxylative Csp³–N bond formation via electrochemical oxidation†

Zhimin Xu,‡^a Yue Zheng,‡^a Zhihui Wang,^a Xiaoqing Shao,^a Lifang Tian*^a and Yahui Wang

*^a

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* Corresponding authors

^a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China
E-mail: tianlifang@njtech.edu.cn, ias_yhwang@njtech.edu.cn

Abstract

A dehydroxylative Csp³–N coupling reaction assisted by triphenylphosphine has been developed through electrochemical oxidation. The reaction proceeds via anodic oxidation of triphenylphosphine to generate its corresponding radical cation, followed by reacting with hydroxyl groups to form alkoxy triphenylphosphonium ions, which are trapped by azoles or amides to construct C–N bonds. This method provides an efficient electrochemical strategy of activating hydroxyl groups to form C–N bonds under mild conditions.

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Article information

DOI: https://doi.org/10.1039/C9CC08622F
Article type: Communication
Submitted: 05 Nov 2019
Accepted: 22 Nov 2019
First published: 22 Nov 2019

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Chem. Commun., 2019,55, 15089-15092

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Triphenylphosphine-assisted dehydroxylative Csp³–N bond formation via electrochemical oxidation

Z. Xu, Y. Zheng, Z. Wang, X. Shao, L. Tian and Y. Wang, Chem. Commun., 2019, 55, 15089 DOI: 10.1039/C9CC08622F

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