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Heterogeneous Gold‐Catalyzed Selective Reductive Transformation of Quinolines with Formic Acid
Author(s) -
Tao Lei,
Zhang Qi,
Li ShuShuang,
Liu Xiang,
Liu YongMei,
Cao Yong
Publication year - 2015
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.201400721
Subject(s) - chemistry , quinoline , chemoselectivity , formic acid , catalysis , formylation , combinatorial chemistry , regioselectivity , substrate (aquarium) , colloidal gold , organic chemistry , nanoparticle , nanotechnology , oceanography , materials science , geology
Single phase rutile titania supported gold nanoparticles (Au/TiO 2 ‐R) are found to be efficient and versatile catalysts for chemo‐ and regioselective transfer hydrogenation of quinoline derivatives to 1,2,3,4‐tetrahydroquinolines (THQs) using formic acid (FA) as a safe and convenient hydrogen source under mild conditions. The activity and chemoselectivity of the Au/TiO 2 ‐R catalyst towards THQs is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Furthermore, a straightforward and selective route to N ‐formyltetrahydroquinolines (FTHQ) directly from quinoline compounds and FA by one‐pot, gold‐catalyzed reductive N‐formylation protocol is also established.