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A Heterogeneous Iridium Catalyst for the Hydroboration of Pyridines
Jessica Rodriguez1, Matthew P Conley1
1Department of Chemistry, University of California, Riverside, California 92521, United States.
Abstract:
Sulfated zirconium oxide (SZO) capped with silylium-like ions reacts with (cod)Ir(py)Cl (cod = 1,5-cyclooctadiene; py = pyridine) to form [Ir(cod)py][SZO] (1) and Me3SiCl. 1 can also be formed in reactions of phosphonium functionalized SZO and [Ir(cod)(OSi(OBu)3]2, which forms [Ir(cod)P(Bu)2Ph][SZO] (2), followed by reaction with pyridine to form 1. FTIR and 15N{1H} MAS NMR spectroscopy are consistent with coordination of pyridine in 1 to an electrophilic iridium. 1 is moderately active in the dearomative hydroboration of pyridine. The primary product of this reaction is 1,2-dihydropyridine, which converts to the 1,4-dihydropyridine product at long reaction times. 1 catalyzes the dearomative hydroboration of a variety of substituted pyridines and is also reactive toward pyrazines and N-methylimidazole.
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