Rhodium(iii)-catalyzed C-H activation at the C4-position of indole: switchable hydroarylation and oxidative Heck-type reactions of maleimides

Chemical Communications : Chem Comm
Mahadev Sharanappa SherikarKandikere Ramaiah Prabhu

Abstract

A Rh(iii)-catalyzed C-H activation of indole at the C4-position leading to novel and switchable functionalization has been reported by employing a weakly co-ordinating COCF3 group as a directing group. An additive plays an important role in switching the selectivity between 1,4-addition products and Heck-type products. An acid additive led to the formation of 1,4-addition products whereas a base additive promotes the formation of Heck-type products. Deuteration studies and control experiments were helpful to propose the mechanism.

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Citations

Apr 4, 2020·Organic & Biomolecular Chemistry·Asim Kumar GhoshAlakananda Hajra
Oct 10, 2020·Chemical Communications : Chem Comm·Bo JiangXiaobo Yang
Nov 10, 2020·Chemistry, an Asian Journal·Sourav PradhanTharmalingam Punniyamurthy
Apr 22, 2021·The Journal of Organic Chemistry·Ankita ThakurUpendra Sharma
May 20, 2021·Organic & Biomolecular Chemistry·Dhananjay S NipateAnil Kumar
Jun 25, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Tanumay SarkarTharmalingam Punniyamurthy
Jan 29, 2019·Organic Letters·Nachimuthu Muniraj, Kandikere Ramaiah Prabhu
Nov 26, 2019·The Journal of Organic Chemistry·Yu-Chao YuanRafael Gramage-Doria
Jul 13, 2019·Organic Letters·Fuzhong HanXiangping Hu
Jan 30, 2020·The Journal of Organic Chemistry·Xinxia ShiMin Wang
Mar 21, 2020·The Journal of Organic Chemistry·Mahadev Sharanappa SherikarKandikere Ramaiah Prabhu
Sep 7, 2021·Chemical Society Reviews·B PrabagarZhuangzhi Shi

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