Transfer hydrogenation of ketones catalyzed by complexes of ruthenium(II) with the heterotridentate [P,N,O] ligands (S)-2-[{2-(diphenylphosphanyebenzylidene}amino]propan-1-ol, (S)-2-[{2-(diphenylphosphanyl)benzyl}amino]propan-1-ol or the [P,N,S] ligand (S)-2-(dimethylamino)-1-(diphenylphosphino)-3-(methylthio)propane

被引:8
|
作者
Obaid, Abeer H. [1 ]
Stracey, Nuru G. [1 ,2 ]
Incarvito, Christopher D. [1 ,3 ]
Mercado, Brandon Q. [1 ,4 ]
Parr, Jonathan [1 ]
机构
[1] Yale Univ, Dept Chem, Sterling Chem Labs, 225 Prospect St, New Haven, CT 06520 USA
[2] Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA
[3] Yale Univ, Res Operat & Technol, West Campus,100 West Campus Dr, Orange, CT 06477 USA
[4] Yale Univ, Dept Chem, Chem & Biol Instrument Ctr, 225 Prospect St, New Haven, CT 06520 USA
关键词
Transfer hydrogenation; Ruthenium; Heterotridentate ligands; Dimethylamine borane; X-ray crystallography; ASYMMETRIC TRANSFER HYDROGENATION; BORANE-AMINE ADDUCTS; SCHIFF-BASE LIGANDS; DONOR SETS; DIMETHYLAMINE-BORANE; CARBONYL-COMPOUNDS; CRYSTAL-STRUCTURES; AMMONIA-BORANE; DEHYDROGENATION; REDUCTION;
D O I
10.1016/j.jorganchem.2016.12.008
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ruthenium complexes [mer-kappa(3)-[(S)-Ph2PC6H4CH = NCH(CH3)CH2OH)PPh3RuCl2-P,N,O] 1, [mer-kappa(3)-{(S)-Ph2PC6H4CH2NHCH(CH3)CH2OH)PPh3RuCl2- P,N,O] 2 and R(S)-Ph2PCH2C(H)N(CH3)(2)CH2SCH3}PPh3RuCl2] 3 have been prepared and their activity in the catalytic transfer hydrogenation 9f ketones investigated. Using isopropanol-isopropoxide as the hydrogen donor, 1.0PPh(3).toluene and 2.OPPh3.CH2Cl2 both showed low activity with average turnover frequency up to 1.1 per hour and enantiomeric excess up to 39.9% where 3 showed no activity. With dimethylamine borane as the hydrogen donor, 1.0PPh3.toluene and 3 proved active catalysts showing average activity up to 3.0 turnovers per hour and selectivity up to 46% ee. New structural information on [(HNMe2)(2)BH2]Cl, a side product in the reaction, is presented. (C) 2016 Elsevier B.V. All rights reserved.
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页码:74 / 84
页数:11
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