Intramolecular Metal‐Free Oxidative Aryl–Aryl Coupling: An Unusual Hypervalent‐Iodine‐Mediated Rearrangement of 2‐Substituted N‐Phenylbenzamides |
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| Authors: | Siyun Shang Dr Daisy Zhang‐Negrerie Prof?Dr Yunfei Du Prof?Dr Kang Zhao |
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| Institution: | 1. Tianjin Key Laboratory for Modern Drug Delivery & High‐Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072 (China);2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072 (China) |
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| Abstract: | Hypervalent‐iodine‐mediated oxidative coupling of the two aryl groups in either 2‐acylamino‐N‐phenyl‐benzamides or 2‐hydroxy‐N‐phenylbenzamides, with concomitant insertion of the ortho‐substituted N or O atom into the tether, has been described for the first time. This unusual metal‐free rearrangement reaction involves an oxidative C(sp2)? C(sp2) aryl–aryl bond formation, cleavage of a C(sp2)? C(O) bond, and a lactamization/lactonization. Furthermore, unsymmetrical diaryl compounds can be easily obtained by removing the tether within the cyclized product. |
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| Keywords: | cross‐coupling heterocycles hypervalent iodine reagents rearrangement |
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