Stereocontrolled Synthesis of Benzo[k]fluoranthenes—An Unexpected Isomerization Mediated by Rhodacyclopentadiene

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期刊

Chemistry - A European Journal


标题

Stereocontrolled Synthesis of Benzo[k]fluoranthenes—An Unexpected Isomerization Mediated by Rhodacyclopentadiene


作者

Shengjie Xu,Kejuan Chen,Prof. Dr. Hui Chen,Prof. Dr. Jiannian Yao,Prof. Dr. Xiaozhang Zhu


摘要

An Unexpected Isomerization In their Communication onpage 16442 ff., H. Chen, X. Zhu, and co-workers investigate controllable stereochemistry in the RhIII-catalyzed synthesis of benzo[k]fluoranthenes. The experimental results, combined with theoretical mechanism investigations, suggest that E/Z isomerization occurs for substrates bearing electron-withdrawing groups (EWG; EDG=electron-donating groups) and that the reaction is mediated by rhodacyclopentadienes. This CC isomerization, controlled by the electronic properties of the substituents, was demonstrated for the first time in transition-metal-catalyzed annulation reactions. This work unravels the importance of locked rhodacycles on the stereochemical specificity of RhIII-catalyzed annulation reactions.


原文链接

http://onlinelibrary.wiley.com/doi/10.1002/chem.201485061/abstract

2017年02月08日

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