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Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration
Author(s) -
Wang Yong,
Cao Xinyi,
Zhao Leyao,
Pi Chao,
Ji Jingfei,
Cui Xiuling,
Wu Yangjie
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000759
Subject(s) - chemistry , chemoselectivity , benzonitrile , transfer hydrogenation , acetophenone , benzaldehyde , phenylsilane , catalysis , nitrile , nitrobenzene , organic chemistry , hydrogenolysis , photochemistry , combinatorial chemistry , medicinal chemistry , ruthenium
A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H 2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene>diphenylmethanimine>benzaldehyde>azobenzene>nitrobenzene>quinoline>acetophenone>benzonitrile . Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano‐palladium catalyst in situ generated from Pd(OAc) 2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti‐Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D 2 O and HBPin via in situ HD generation and discrimination.