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Nickel-Catalyzed Electrochemical Reductive Homocouplings of Aryl and Heteroaryl Halides: A Useful Route to Symmetrical Biaryls
Synthesis ( IF 2.6 ) Pub Date : 2017-09-12 , DOI: 10.1055/s-0036-1589100
Stéphane Sengmany , Eric Léonel , Rima Rahil , Erwan Le Gall

Abstract

Due to their widespread presence in functional materials and pharmaceuticals, biaryls are of fundamental importance in organic chemistry. Methods for the synthesis of symmetrical biaryls generally involve both metallic reduction and transition-metal catalysis. In this work, we show that electroreduction can also constitute a very relevant way to achieve the nickel-catalyzed reductive synthesis of symmetrical biaryl compounds. Therefore, it is demonstrated that both aryl and heteroaryl halides undergo reductive coupling to furnish the corresponding symmetrical biaryls in fair to excellent yields. Reactions are performed under very mild conditions thus ensuring important functional group tolerance.

Due to their widespread presence in functional materials and pharmaceuticals, biaryls are of fundamental importance in organic chemistry. Methods for the synthesis of symmetrical biaryls generally involve both metallic reduction and transition-metal catalysis. In this work, we show that electroreduction can also constitute a very relevant way to achieve the nickel-catalyzed reductive synthesis of symmetrical biaryl compounds. Therefore, it is demonstrated that both aryl and heteroaryl halides undergo reductive coupling to furnish the corresponding symmetrical biaryls in fair to excellent yields. Reactions are performed under very mild conditions thus ensuring important functional group tolerance.



中文翻译:

芳基卤和杂芳基卤化物的镍催化电化学还原均偶联:对称联芳基的有用途径

摘要

由于它们在功能材料和药物中的广泛存在,联芳基在有机化学中至关重要。合成对称联芳基的方法通常包括金属还原和过渡金属催化。在这项工作中,我们表明电还原也可以构成实现镍催化对称联芳基化合物还原合成的一种非常相关的方法。因此,证明了芳基卤和杂芳基卤都经过还原偶联,以公平至优异的产率提供了相应的对称联芳基。反应在非常温和的条件下进行,因此可确保重要的官能团耐受性。

由于它们在功能材料和药物中的广泛存在,联芳基在有机化学中至关重要。合成对称联芳基的方法通常包括金属还原和过渡金属催化。在这项工作中,我们表明电还原也可以构成实现镍催化对称联芳基化合物还原合成的一种非常相关的方法。因此,证明了芳基卤和杂芳基卤都经过还原偶联,以公平至优异的产率提供了相应的对称联芳基。反应在非常温和的条件下进行,因此可确保重要的官能团耐受性。

更新日期:2017-09-12
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