Aerobic oxidation of primary alcohols catalyzed by copper complexes of 1,10-phenanthroline-derived ligands |
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Authors: | Oindrila Das Tapan Kanti Paine |
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Institution: | Department of Inorganic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, India. ictkp@iacs.res.in. |
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Abstract: | Five copper complexes (L(1))(2)Cu(H(2)O)](ClO(4))(2) (1), (L(1))Cu(H(2)O)(3)](ClO(4))(2) (1a), (L(3))(2)Cu(H(2)O)](ClO(4))(2) (2), (L(5))(2)Cu(H(2)O)](ClO(4))(2) (3) and (L(6))(2)Cu](ClO(4)) (4) (where L(1) = 1,10-phenanthroline, L(3) = 1,10-phenanthroline-5,6-dione, L(5) = 1,10-phenanthrolinefuroxan and L(6) = 2,9-dimethyl-1,10-phenanthrolinefuroxan), and in situ prepared copper complexes of 2,9-dimethyl-1,10-phenanthroline (L(2)) or 2,9-dimethyl-1,10-phenanthrolinedione (L(4)) were used for aerial oxidation of primary alcohols to the corresponding aldehydes under ambient conditions. The copper catalysts have been found to catalyze a series of primary alcohols including one secondary alcohol with moderate turnover numbers and selectivity towards primary alcohols. Copper(ii) complexes 1 (or 1a) and 2 were found to be the better catalysts among all other systems explored in this study. A copper(ii)-superoxo species is implicated to initiate the oxidation reaction. Structural and electronic factors of 1,10-phenanthroline-based ligands affecting the catalytic results for aerial oxidation of alcohols are discussed. |
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