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Organometallics
Volumn 27, Issue 13, 2008, Pages 2898-2901
Exceptionally efficient unsymmetrical ruthenium(II) NNN complex catalysts bearing a pyridyl-based pyrazolyl-imidazolyl ligand for transfer hydrogenation of ketones
Author keywords

[No Author keywords available]
Indexed keywords

BEARINGS (STRUCTURAL); CATALYSIS; HYDROGENATION; KETONES; LIGANDS; ORGANIC COMPOUNDS; RUTHENIUM;
EID: 47949096754     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8002043     Document Type: Article
Times cited : (84)
References (54)
  • 1
    • 38049002421 scopus 로고    scopus 로고
    • For selected recent reviews, see: a
    • For selected recent reviews, see: (a) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300.
    • (2007) J. Acc. Chem. Res , vol.40 , pp. 1300
    • Ikariya, T.1    Blacker, A.2
  • 42
    • 47949088381 scopus 로고    scopus 로고
    • 2Cl2/ethyl acetate, 3/1 v/v), affording compound 3a as a pale yellow solid (4.80 g, 71%) (see the Supporting Information).
    • 2Cl2/ethyl acetate, 3/1 v/v), affording compound 3a as a pale yellow solid (4.80 g, 71%) (see the Supporting Information).
  • 43
    • 47949114290 scopus 로고    scopus 로고
    • 3 (0.48 g, 0.50 mmol) and benzoimidazole 3a (0.15 g, 0.50 mmol) in toluene (40 mL) was refluxed for 2 h, giving a red-brown microcrystalline solid. The mixture was cooled to ambient temperature, and the solid was filtered off, washed with diethyl ether (3 × 50 mL), and dried under vacuum to afford complex 4a (0.33 g, 91%) as a red-brown crystalline solid (see the Supporting Information).
    • 3 (0.48 g, 0.50 mmol) and benzoimidazole 3a (0.15 g, 0.50 mmol) in toluene (40 mL) was refluxed for 2 h, giving a red-brown microcrystalline solid. The mixture was cooled to ambient temperature, and the solid was filtered off, washed with diethyl ether (3 × 50 mL), and dried under vacuum to afford complex 4a (0.33 g, 91%) as a red-brown crystalline solid (see the Supporting Information).
  • 44
    • 47949120200 scopus 로고    scopus 로고
    • Crystal data for 4b · CH3OH: C37H 36Cl2N5PORu, monoclinic, Cc, a, 14.5821(12) Å, b= 15.1108(12) Å, c= 15.6511(13) Å, α, γ, 90°, β, 104.7770(10)°, V, 3334.6(5) Å3 Z, 4, T, 293(2) K, Dcalcd, 1.533 g cm3, R(F, 5.06% for 4726 observed reflections (2.96 ≤ 20θ ≤ 54.00°, Crystal data for 6: C37H35ClN5OPRuS, monoclinic, P21,/n, a, 16.3548(12) Å, b= 11.1683(8) Å, c= 19.8291(14) Å, α, γ, 90°, β= 107.6350(10)°, V, 3451.7(4) Å3, Z, 4, T= 293(2) K, Dcalcd, 1-473 g cm -3, R(F, 4.60% for 7506 observed reflections 2.86 ≤ 2θ ≤ 54.00°
    • -3, R(F) = 4.60% for 7506 observed reflections (2.86 ≤ 2θ ≤ 54.00°).
  • 45
    • 47949132400 scopus 로고    scopus 로고
    • A typical catalytic procedure is given. Transfer hydrogenation of acetophenone: the catalyst solution A was prepared by dissolving complex 4a (7.2 mg, 10.0 μmol) in 2-propanol (198.0 mL). Under a nitrogen atmosphere, a mixture of acetophenone (0.240 g, 2.0 mmol) and 19.8 mL of the catalyst solution A containing 1.0 μmol of complex 4a was stirred at 82°C for 5 min. A 0.2 mL portion of 0.1 M iPrOK (0.02 mmol) solution in 2-propanol was then introduced to initiate the TH of the ketone. At the stated time, 0.05-0.1 mL of the reaction mixture was immediately sampled and diluted with 0.5 mL of 2-propanol at ambient temperature for GC analysis (see the Supporting Information).
    • A typical catalytic procedure is given. Transfer hydrogenation of acetophenone: the catalyst solution A was prepared by dissolving complex 4a (7.2 mg, 10.0 μmol) in 2-propanol (198.0 mL). Under a nitrogen atmosphere, a mixture of acetophenone (0.240 g, 2.0 mmol) and 19.8 mL of the catalyst solution A containing 1.0 μmol of complex 4a was stirred at 82°C for 5 min. A 0.2 mL portion of 0.1 M iPrOK (0.02 mmol) solution in 2-propanol was then introduced to initiate the TH of the ketone. At the stated time, 0.05-0.1 mL of the reaction mixture was immediately sampled and diluted with 0.5 mL of 2-propanol at ambient temperature for GC analysis (see the Supporting Information).

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