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Cycloruthenation of N ‐(Naphthyl)salicylaldimine and Related Ligands: Utilization of the Ru–C Bond in Catalytic Transfer Hydrogenation
Author(s) -
Dutta Jayita,
Richmond Michael G.,
Bhattacharya Samaresh
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201402236
Subject(s) - chemistry , transfer hydrogenation , catalysis , ruthenium , medicinal chemistry , cyclic voltammetry , crystal structure , stereochemistry , redox , crystallography , electrochemistry , inorganic chemistry , organic chemistry , electrode
Upon reaction with [Ru(PPh 3 ) 2 (CO) 2 Cl 2 ], N ‐(naphthyl)‐4‐R‐salicylaldimines (R = OCH 3 , H, Cl; H 2 L 1 –H 2 L 3 ) and 2‐hydroxy‐ N ‐(naphthyl)naphthaldimine (H 2 L 4 ) readily undergo cycloruthenation by C–H bond activation at the peri position to afford complexes of the type [Ru(PPh 3 ) 2 ( L )(CO)] ( L = L 1 – L 4 ). The crystal structures of the [Ru(PPh 3 ) 2 ( L )(CO)] ( L = L 1 , L 2 , L 4 ) complexes were determined and the structure of [Ru(PPh 3 ) 2 ( L 3 )(CO)] optimized by DFT calculations. The thermodynamics for the reaction of [Ru(PPh 3 ) 2 (CO) 2 Cl 2 ] with H 2 L 2 to give [Ru(PPh 3 ) 2 ( L 2 )(CO)] were determined. All the complexes show intense absorptions in the visible and UV regions, which have been analyzed by TDDFT calculations. Cyclic voltammetry of the four cycloruthenated complexes showed two oxidations within the range 0.50–1.35 V versus SCE and a reduction at around –1.75 V versus SCE. The [Ru(PPh 3 ) 2 ( L )(CO)] ( L = L 1 – L 4 ) complexes were found to efficiently catalyze the transfer hydrogenation of carbonyl compounds.