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Designing Vasicine‐Derived Ligands and Their Application for Ruthenium‐Catalyzed Transfer Hydrogenation Reactions in Water: Synthesis of Amines and Alcohols
Author(s) -
Sharma Sushila,
Kumar Manoranjan,
Nayal Onkar S.,
Thakur Maheshwar S.,
Bhatt Vinod,
Kumar Neeraj,
Singh Bikram,
Sharma Upendra
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600384
Subject(s) - ruthenium , chemistry , transfer hydrogenation , catalysis , sodium formate , reductive amination , amine gas treating , organic chemistry , amination , formate , noyori asymmetric hydrogenation , combinatorial chemistry , ammonium formate , acetonitrile
Six quinazoline ligands (i.e., 3 – 8 ) were synthesized by starting from vasicine and vasicinone, and their applications towards ruthenium‐catalyzed transfer hydrogenation reactions were evaluated. The 3 /[RuCl 2 ( p ‐cymene)] 2 catalytic system was assessed for its use in the ruthenium‐catalyzed transfer hydrogenation reaction of aldehydes, ketones, and imines to give the corresponding alcohols and amines and also assessed for its use in the direct reductive amination of carbonyl compounds with anilines. The 3 /[RuCl 2 ( p ‐cymene)] 2 catalytic system demonstrated good to excellent activity in water with sodium formate as the hydrogen source. Current studies have revealed that among all of the synthesized ligands, those that have secondary amine groups and a rigid backbone are more active towards transfer hydrogenation reactions of unsaturated compounds.