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Rhodium-Catalyzed C-H Activation of Phenacyl Ammonium Salts Assisted by an Oxidizing C-N Bond: A Combination of Experimental and Theoretical Studies

Songjie Yu, Song Liu, Yu Lan*, Boshun Wan* and Xingwei Li*

*Chinese Academy of Sciences, Dalian 116023; Chongqing University, Chongqing 400030, China, Email: xwlidicp.ac.cn, lanyucqu.edu.cn, bswandicp.ac.cn

S. Yu, S. Liu, Y. Lan, B. Wan, X. Li, J. Am. Chem. Soc., 2015, 137, 1623-1631.

DOI: 10.1021/ja511796h


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Abstract

α-Ammonium acetophenones with an oxidizing C-N bond can serve as substrates for Rh(III)-catalyzed C-H activation under redox-neutral conditions. The coupling with α-diazo esters afforded benzocyclopentanones, and the coupling with unactivated alkenes such as styrenes and aliphatic olefins gave ortho-olefinated acetophenoes. In both systems the reactions proceeded with a broad scope, high efficiency, and functional group tolerance.


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Key Words

indanones


ID: J48-Y2015