Organic & biomolecular chemistry

Synthetic and mechanistic studies of metal-free transfer hydrogenations applying polarized olefins as hydrogen acceptors and amine borane adducts as hydrogen …

X Yang, T Fox, H Berke

Index: Yang, Xianghua; Fox, Thomas; Berke, Heinz Organic and Biomolecular Chemistry, 2012 , vol. 10, # 4 p. 852 - 860

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Citation Number: 35

Abstract

Metal-free transfer hydrogenation of polarized olefins (RR′ CCEE′: R, R′= H or organyl, E, E′= CN or CO2Me) using amine borane adducts RR′ NH–BH3 (R= R′= H, AB; R= Me, R′= H, MAB; R= tBu, R′= H, tBAB; R= R′= Me, DMAB) as hydrogen donors, were studied by means of in situ NMR spectroscopy. Deuterium kinetic isotope effects and the traced hydroboration intermediate revealed that the double H transfer process occurred ...