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Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates
Angewandte Chemie International Edition ( IF 11.994 ) Pub Date : 2017-12-28 , DOI: 10.1002/anie.201710931
Yi-Hung Chen, Simon Graßl, Paul Knochel

Abstract

Aryl- and heteroarylzinc pivalates can be aminated with O-benzoylhydroxylamines at 25 °C within 2–4 h in the presence of 2.5–5.0 % CoCl2⋅2 LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56 % overall yield by using this cobalt-catalyzed amination as the key step.

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Animating aminations: A range of aryl- and heteroarylzinc pivalates underwent cobalt-catalyzed electrophilic aminations with O-benzoylhydroxylamines in good yields under mild conditions. This reaction can be applied to prepare arylamines and diarylamines. A new tuberculosis drug candidate was prepared in six steps and 56 % overall yield by using the cobalt-catalyzed amination as the key step.

更新日期:2018-01-03

 

Some contents have been Reproduced with permission of the American Chemical Society.
Some contents have been Reproduced by permission of The Royal Society of Chemistry.
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