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Synlett

Volumn , Issue 2, 2009, Pages 271-275

Nucleophilic homogeneous hydrogenation by iridium complexes

(3) Semeniuchenko, Volodymyr a,b Khily, Volodymyr b Groth, Ulrich a

a UNIVERSITY OF KONSTANZ (Germany)

b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV (Ukraine)

Author keywords

Alkenes; Complexes; Homogenous catalysis; Hydrogenation; Iridium

Indexed keywords

EID: 62349131170 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087513 Document Type: Article

Times cited : (18)

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- Typical Experimental Procedure: Catalyst (1-2 mg) was weighed into a Teflon vessel, then a calculated amount of substrate (catalyst/substrate, 1:100, a few drops of thiophene (to suppress possible heterogeneous process, base (0.07 mL) and degassed solvent (5 mL, distilled under an N2 atmosphere) were added. All operations were quickly carried out under air and the vessel was sealed up in stainless steel autoclave. The autoclave was first purged with H2 (3 x) and then charged to 100 bar. After 8 h of hydrogenation at r.t, the autoclave was unsealed and the reaction mixture was subjected to gas chromatography with mass-spectral analyser GCMS, GC conversion was calculated from correspondent peak areas and was not corrected with an external standard. If needed, the reaction mixture was evaproated in vacuo, the residue dissolved in CDCl3 or DMSO-d6 and subjected to 1H NMR analysis, which showed the same conversion
- 1H NMR analysis, which showed the same conversion.

20
- 62349107290
- To a solution of 8-hydroxyquinoline (23.4 mg, 0.162 mmol) in Et 2O (1 mL) n-BuLi (0.1 mL, 0.16 mmol, 1.6 M hexane solution) was added. After stirring for 10 min Ph2PCl (36.5 mg, 0.162 mmol) was added and stirred for 2 h. The Et2O was evaporated, and [IR (cod)Cl]2 (54.2 mg, 0.081 mmol) in CH2Cl2 (2 mL) added. The mixture obtained was refluxed for 2 h, cooled, and sodium tetrakis[3,5-bis(trifluoromethyl)-phenyl]borate (NaBARF; 143.2 mg, 0.162 mmol) was added. After overnight stirring the iridium [8-(diphenylphosphinooxy) quinoline](1,5-cyclooctadiene) tetrakis-[3,5-bis(trifluoromethyl)phenyl]borate was separated by silica gel column chromatography Rf 0.9; CH2Cl2, This complex decomposed after its formation, and could not be isolated in pure form at r.t. This product was characterized by 31P NMR, having only one peak at δ, 107 ppm. During 1 d it could catal
- 2.

21
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- To a solution of [IR(cod)Cl]2 (30.1 g, 0.044 mmol) and NaBARF (77.4 mg, 0.088 mmol) in CH2Cl2 (1.5 mL) freshly distilled 1.5-cyclooctadiene (0.1 mL) was added. The mixture was stirred for 30 min, then Na2SO4 was added to adsorb the formed NaCl. The mixture was filtrated, thoroughly washed by CH2Cl2, evaporated to 0.25 mL and pentane (10 mL) was added. The formed crystalline iridium bis(1,5-cyclooctadiene)tetrakis [3,5-bis(trifluoromethyl)-phenyl]borate, IR(cod)2]BARF) was collected by filtration, washed from the filter by CH2Cl2 and dried under vacuum. 1H NMR (400 MHz, CDCl3/TMS, δ, 2.26 (m, 8 H, CH2, 2.41 (m, 8 H CH2, 5.00 (s, 8 H, CHCOD, 7.56 (s, 4 H, 4-HBARF, 7.71 (s, 8 H, 2-HBARF and 6-HBARF, Under nitrogen to a suspension of 1,3-dimethyl-1H-imidazol-3-ium iodide 23.1 mg, 0.10
- 3): δ = -62.8.

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29
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- 3-Trifluoroacetylchromone, mixture of ketone and hydrate, was obtained as a gift from A. Kotljatrov and V. Iaroshenko, or synthesized by the known procedure.21 This mixture (0.8 g) was stirred with P 2O5 (4.7 g) in CH2Cl2 (50 mL) for 30 h (control by 19F NMR, and then filtrated under nitrogen. The filtrate was evaporated and dried under high vacuum, to give 10 (0.3 g, 1H NMR data were similar to those published.19 13C NMR (100 MHz, CDCl3/TMS, δ, 115.73 (q, J, 289.4 Hz, CF3, 118.34 (8-CH, 119.14, 3-CH, 124.87 (10-C, 126.65 (5-CH, 127.09 (6-CH, 135.04 (7-CH, 155.551 (9-C, 163.07 (q, J, 2.2 Hz, 2-CH, 172.65 (4-C, 179.38 (q, J, 39.2 Hz, COCF3, 19F NMR 376 MHz, CDCl3/ CFCl3, δ, 74.81
- 3): δ = -74.81.

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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.