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Regioselective homogeneous hydrogenation of heteroaromatic nitrogen compounds by use of [RuH(CO)(NCMe)2(PPh3)2]BF4 as the precatalyst
Authors:Merlin Rosales  Janeth Navarro  Ligbel Sánchez  Angel González  Ysaías Alvarado  Raúl Rubio  Carlos De La Cruz  Tamara Rajmankina
Institution:(1) Inorganic Chemistry Laboratory, Facultad de Ciencias, La Universidad del Zulia (LUZ), Apdo. 526, Maracaibo, Venezuela;(2) Molecular and Atomic Spectroscopy Laboratory, Facultad de Ciencias, La Universidad del Zulia (LUZ), Apdo. 526, Maracaibo, Venezuela
Abstract:Summary The complex RuH(CO)(NCMe)2(PPh3)2]BF4 (1) is an efficient and regioselective catalyst precursor for the hydrogenation of polyaromatic nitrogen compounds such as quinoline (Q), isoquinoline (iQ), indole (ln), 5,6- and 7,8-benzoquinoline (BQ) and acridine (A) under relatively mild reaction conditions (125 °C, 4 atm H2). The order of individual initial rates was: A > Q > 5,6-BQ > 7,8-BQ > ln > iQ, reflecting both steric and electronic effects. For the regioselective homogeneous hydrogenation of A to 9,10-dihydroacridine (DHA) catalysed by complex (1), a kinetic study was carried out; the experimentally determined rate law was r = k 1 Ru] H2]. These findings are consistent with a mechanism involving the hydrogenation of RuH(CO)(A)(NCMe)(PPh3)2]BF4 to yield DHA and the unsaturated species RuH(CO)(NCMe)(PPh3)2]BF4 in the rate-determining step.
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