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Peng Bo in 'Angew'
Post Time: 05/06/2018

      Peng Bo, the leader of the Organic Fluorine Chemistry Institute at Zhejiang Normal University, and his team, including Dr. Xin Huang, published an article in the international academic journal Angewandte Chemie titled “Selective ortho C‐H Cyanoalkylation of (Diacetoxyiodo)arenes via [3,3]‐Sigmatropic Rearrangement” (dx.doi.org/10.1002/anie.201803455). Angewandte Chemie (meaning ‘Applied Chemistry’) is an international top-level chemistry journal that is published by Wiley-VCH. The journal appears in two editions: a German edition and an English edition. This journal contains research articles covering fields ranging from organic chemistry, materials science, to polymer chemistry. The impact factor for 2016-2017 is 11.9.

       This study follows another breakthrough achieved by the team and published in the Journal of the American Chemical Society in 2017 involving rapid electrophilic rearrangement with aryl sulfoxides (DOI: 10.1021/jacs.7b00969). ZNU’s graduate student Tian Junsong is the first author of the article, and Wang Zhixiang, researcher at the Chinese Academy of Sciences, is co-corresponding author. Wang and his grad student Zhang Chaoshen led his team in contributing to the theoretical calculations involved in this study.

 

J. Am. Chem. Soc. 2017, 139, 4211.

Angew. Chem. Int. Ed. 10.1002/anie.201803455

 

       Hypervalentiodine reagents have unique oxidation properties and have long been used in synthetic chemistry. Such reagents are often used as oxidants or electrophilic aryl sources in reactions, after which aryl iodide or iodine atoms are discarded. In recent years, an aryliodane involved rearrangement reaction has been developed. In comparison with traditional hypervalent iodine chemistry, this type of reactions not only realizes the functionalization of the ortho-position of the aryliodanes but also maintains the iodine atoms within products, providing a new direction for hypervalent iodine chemistry. But, for a long time, this kind of reaction was generally limited by a narrow substrate scope, poor selectivity, and relatively low yield. These issues are probably due to the lack of reliable means for precisely controlling the reactivity of highly reactive aryliodane species.

       Inspired by a Chinese proverb saying, “In the world of kungfu, only a speedy act is invincible,” the research team got rid of the traditional approach relied on lowly-reactive nucleophiles and switched to highly-reactive α-Sn alkylnitrile. By doing so, the reaction could be completed in a short time (within 5 mins), largely increasing the selectivity of reaction, and thus providing a new strategy for aryliodane involved rearrangement reactions.

       The study was funded by the National Natural Science Foundation of China and the Qianjiang Scholar Program of the Zhejiang Province. (Translated by Marco Lovisetto, edited by Xiamara Hohman and revised by Prof. Peng Bo)

 

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