Dinuclear ruthenium(I) complexes of the type [Ru2(CO)4L2] with carboxylate or 2-pyridonate ligands: Evaluation as catalysts for olefin cyclopropanation with diazoacetates |
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| Institution: | 1. Área Química Inorgánica, DEC, Facultad de Química, Universidad de la República, Montevideo, Uruguay;2. Dipartimento di Chimica, Università degli Studi di Firenze, Sesto Fiorentino, Italy;3. Departament de Química Inorgànica/Institut de Ciència Molecular, Facultat de Química de la Universitat de València, València, Spain;1. Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Pr. Oktyabrya, Ufa 450075, Russian Federation;2. Chemistry, University of Southampton, Southampton SO17 1BJ, United Kingdom;1. Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA;2. Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA;1. School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional Aggregated Materials, Ministry of Education, Shandong University, Shanda Nanlu 27, Jinan 250199, PR China;2. Shandong Provincial Key Laboratory of Fine Chemicals, Qilu University of Technology, Jinan 250353, PR China;3. Department of Applied Chemistry, College of Chemistry, Shandong Normal University, Jinan 250014, PR China |
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| Abstract: | Dinuclear ruthenium(I,I) carboxylate complexes Ru2(CO)4(μ-OOCR)2]n (R = CH3 (1a), C3H7 (1b), H (1c), CF3 (1d)) and 2-pyridonate complex Ru2(CO)4(μ-2-pyridonate)2]n (3) catalyze efficiently the cyclopropanation of alkenes with methyl diazoacetate. High yields are obtained with terminal nucleophilic alkenes (styrene, ethyl vinyl ether, α-methylstyrene), medium yields with 1-hexene, cyclohexene, 4,5-dihydrofuran and 2-methyl-2-butene. The E-selectivity of the cyclopropanes obtained from the monosubstituted alkenes and the cycloalkenes decreases in the order 1b > 1a > 1d > 1c. The cyclopropanation of 2-methyl-2-butene is highly syn-selective. Several complexes of the type Ru2(CO)4(μ-L1)2]2 (4) and (5), Ru2(CO)4(μ-L1)2L2] (L2 = CH3OH, PPh3) (6)–(9) and Ru2(CO)4(CH3CN)2(μ-L1)2] (10) and (11), where L1 is a 6-chloro- or 6-bromo-2-pyridonate ligand, are also efficient catalysts. Compared with catalyst 3, a halogen substituent at the pyridonate ligand affects the diastereoselectivity of cyclopropanation only slightly. |
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