Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides

Organic Letters
Bhanwar Kumar MalviyaSiddharth Sharma

Abstract

This work discloses an electrochemical oxidative cross-coupling of amines with aryl and aliphatic isocyanides. In an undivided cell, the reaction proceeds without involving any transition-metal catalyst, oxidant, or toxic reagents providing carbodiimides in good yields, thereby circumventing stoichiometric chemical oxidants, with H2 as the only byproduct. Moreover, carbodiimides were in situ converted into unsymmetrical ureas in moderate to good yields using an electricity ON-OFF strategy.

References

Apr 1, 1967·Chemical Reviews·F Kurzer, K Douraghi-Zadeh
Aug 1, 1966·Angewandte Chemie·H Ulrich, A A Sayigh
Nov 20, 2004·The Journal of Organic Chemistry·Mianji ZhangPaul R Hanson
Jun 23, 2006·Chemical Society Reviews·Jeffrey B Sperry, Dennis L Wright
Nov 10, 2006·Chemical Reviews·Gilson Zeni, Richard C Larock
Jan 2, 2009·Bioorganic & Medicinal Chemistry Letters·Nian-Yu HuangHong-Wu He
Aug 27, 2011·Chemical Reviews·Ayman El-Faham, Fernando Albericio
Feb 9, 2012·Chemical Communications : Chem Comm·Guanyinsheng QiuJie Wu
Mar 5, 2013·Chemical Society Reviews·Guanyinsheng QiuJie Wu
Aug 1, 2015·Journal of the American Chemical Society·Tatsuya MorofujiJun-ichi Yoshida
Aug 17, 2016·Chemistry : a European Journal·Ming Gong, Jing-Mei Huang
Feb 24, 2017·Environmental Science. Processes & Impacts·Ania S PavittPaul G Tratnyek
Aug 12, 2017·Science·Niankai FuSong Lin
Mar 7, 2018·Angewandte Chemie·Nicolas SauermannLutz Ackermann
Mar 10, 2018·Journal of the American Chemical Society·Xinlong GaoAiwen Lei
Mar 17, 2018·Organic & Biomolecular Chemistry·Kun LiuAiwen Lei
Apr 6, 2018·Chemical Society Reviews·Yating Zhao, Wujiong Xia
Jul 3, 2018·Chemical Reviews·Siegfried R WaldvogelChristopher J Kampf
Jul 12, 2018·Chemical Communications : Chem Comm·Porag Bora, Ghanashyam Bez
Jul 24, 2018·Chemical Communications : Chem Comm·Xing ZhangLinhao Sun
Aug 31, 2018·Journal of the American Chemical Society·Qi-Liang YangTian-Sheng Mei
Mar 22, 2019·Organic & Biomolecular Chemistry·Wolfgang JudDavid Cantillo
Sep 24, 2019·Chemical Communications : Chem Comm·Siyu TianJianbin Chen

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Citations

Jul 9, 2020·Organic & Biomolecular Chemistry·Hai-Tao TangYing-Ming Pan

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