A simple iridicycle catalyst for efficient transfer hydrogenation of N-heterocycles in water

Chemistry : a European Journal
Dinesh TalwarJianliang Xiao

Abstract

A cyclometalated iridium complex is shown to catalyse the transfer hydrogenation of various nitrogen heterocycles, including but not limited to quinolines, isoquinolines, indoles and pyridinium salts, in an aqueous solution of HCO2H/HCO2Na under mild conditions. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), with catalyst loadings as low as 0.01 mol % being feasible. Mechanistic investigation of the quinoline reduction suggests that the transfer hydrogenation proceeds via both 1,2- and 1,4-addition pathways, with the catalytic turnover being limited by the step of hydride transfer.

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Citations

Mar 11, 2017·Chemical Communications : Chem Comm·Chao Wang, Jianliang Xiao
Jun 15, 2017·Organic & Biomolecular Chemistry·Ganesh V More, Bhalchandra M Bhanage
Nov 17, 2017·Chemistry : a European Journal·Alexander S KarnsBas de Bruin
Jan 10, 2020·Chemistry : a European Journal·Timothy James Donohoe, Hamish Hepburn
Sep 6, 2019·Angewandte Chemie·Benjamin M ReevesTimothy J Donohoe
Oct 18, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Xiaofeng WuJianliang Xiao
Aug 12, 2017·Chemistry : a European Journal·Stephen J GeierStephen A Westcott
Sep 26, 2015·Chemistry : a European Journal·Hsin-Yi Tiffany ChenJianliang Xiao
Aug 31, 2016·Topics in Current Chemistry·Martin Wills
Nov 27, 2020·Organic & Biomolecular Chemistry·Jennifer SmithJianliang Xiao
May 4, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Zhenyu ChenJianliang Xiao
Mar 9, 2018·Journal of the American Chemical Society·Yulei WangZheng Huang
Jun 11, 2015·Chemical Reviews·Dong Wang, Didier Astruc

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