Selective partial reduction of quinolines: Hydrosilylation vs. transfer hydrogenation

AM Voutchkova, D Gnanamgari, CE Jakobsche…

Index: Voutchkova, Adelina M.; Gnanamgari, Dinakar; Jakobsche, Charles E.; Butler, Chase; Miller, Scott J.; Parr, Jonathan; Crabtree, Robert H. Journal of Organometallic Chemistry, 2008 , vol. 693, # 10 p. 1815 - 1821

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Citation Number: 47

Abstract

Two mild and versatile catalytic routes give regioselective hydrogenation of the heterocyclic ring of quinoline derivatives avoiding the high pressures of hydrogen required in the conventional hydrogenation route. Hydrosilylation using H3SiPh and catalyzed by [Rh (nbd)(PPh3) 2] PF6 at room temperature gives dihydroquinoline, a product not obtainable via direct hydrogenation. Hydrosilylation of the CN bond of PhCHNPh is also observed ...