Ru (II)-Catalyzed C-H Activation: Ketone-Directed Novel 1,4-Addition of Ortho C-H Bond to Maleimides

Organic Letters
Kiran R BettadapurKandikere Ramaiah Prabhu

Abstract

A 1,4-addition with the nucleophilic center generated at the ortho carbon atom of an aromatic ketone in the presence of the highly reactive α-C-H bond, using a directing group strategy, is presented. The reaction yields pharmaceutically useful 3-arylated succinimide derivatives. In order to gain understanding of this redox neutral reaction, despite the presence of copper acetate, and to substantiate the lack of Heck-type products, DFT calculations have been carried out.

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Citations

Sep 9, 2015·Organic Letters·Veeranjaneyulu LankeKandikere Ramaiah Prabhu
Jun 18, 2016·The Journal of Organic Chemistry·Puspam KeshriKandikere Ramaiah Prabhu
Aug 30, 2016·Organic Letters·Tomohiro MoritaMasahiro Miura
May 24, 2017·Organic Letters·Shengjin SongTeck-Peng Loh
May 26, 2017·Chemical Communications : Chem Comm·Kiran R BettadapurKandikere Ramaiah Prabhu
Jun 1, 2017·The Journal of Organic Chemistry·Nachimuthu Muniraj, Kandikere Ramaiah Prabhu
Jul 27, 2017·Organic Letters·Shuang-Liang LiuMao-Ping Song
Oct 28, 2016·Chemistry : a European Journal·Takanori ShibataKyalo Stephen Kanyiva
Sep 14, 2017·Chemistry : a European Journal·N Y Phani KumarLutz Ackermann
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Sep 20, 2018·Chemical Communications : Chem Comm·Mahadev Sharanappa SherikarKandikere Ramaiah Prabhu
Aug 15, 2018·Angewandte Chemie·Gwilherm Evano, Cédric Theunissen
Jun 3, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Chao DengWeihua Zhang

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