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Highly Active and Selective Ru‐PN H Catalyst in Aerobic Oxidation of Benzyl Amines
Author(s) -
Aman Michal,
Tremmel Jakub,
Dostál Libor,
Erben Milan,
Tydlitát Jiří,
Jansa Josef,
Jambor Roman
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900952
Subject(s) - chemistry , catalysis , phosphine , medicinal chemistry , moiety , ruthenium , ligand (biochemistry) , stereochemistry , organic chemistry , biochemistry , receptor
Set of [Ru(η 6 ‐cymene)(R)XCl] (R=L 1 SnCl, L 1 GeCl L 2 PPh 2 , X=Cl or SnCl 3 , L 1 =[2‐(CH 2 NEt 2 )‐4,6‐( t Bu) 2 C 6 H 2 ] − , L 2 =2,6‐ i Pr 2 ‐C 6 H 3 ‐NH − ) catalysts was tested in aerobic oxidations of primary amines. The activity of studied catalysts depends on the charge of the Ru atom that has been influenced either by donating ligands R or by character of X. Typical Ru/P catalyst [Ru(η 6 ‐cymene)(L 2 PPh 2 )Cl 2 ] ( 3 ) with least negative charge on the Ru atom has been observed as the most effective. The design of the phosphine ligand L 2 containing amino‐phosphine PN H moiety provided efficient anchoring of complex 3 to silica gel via hydrogen bonding of the PN H functional group to SiO 2 to give heterogeneous catalyst 3 ‐ silica . This complex has been also efficiently tested in aerobic oxidation as recyclable catalyst with cumulative TON up to 6930.