Rh(III)-catalyzed C–H olefination of N-pentafluoroaryl benzamides using air as the sole oxidant

Yi Lu, Huai-Wei Wang, Jillian E. Spangler, Kai Chen, Pei-Pei Cui, Yue Zhao, Wei-Yin Sun and Jin-Quan Yu

Chemical Science,
2015, 6, 1923; 10.1039/c4sc03350g


The Yu group from The Scripps Research Institute, in collaboration with the Sun group from Nanjing University, describe a Rhodium(III)-catalyzed C–H olefination transformation, the sole oxidation of which is molecular oxygen.

While these systems have received significant attention in the past, stoichiometric co-oxidants have been required and these conditions often lead to the formation of undesired and difficult to remove by-products.

The Yu group have developed a readily accessible and easily removable electron-withdrawing directing group that has been revealed to be highly effective in this system. In combination with a carbonate base these reaction proceed in near quantitative yields across a broad scope of aromatic substrate for ortho-selective C–H olefination.

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