Hydrogen??Bonding Thiourea Organocatalysts: The Privileged 3, 5??Bis (trifluoromethyl) phenyl Group

…, K Hof, D Gerbig, D Ley, H Hausmann…

Index: Lippert, Katharina M.; Hof, Kira; Gerbig, Dennis; Ley, David; Hausmann, Heike; Guenther, Sabine; Schreiner, Peter R. European Journal of Organic Chemistry, 2012 , # 30 p. 5919 - 5927

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Citation Number: 47

Abstract

Abstract We present evidence that the privileged use of the 3, 5-bis (trifluoromethyl) phenyl group in thiourea organocatalysis is due to the involvement of the ortho-CH bond in the binding event with Lewis-basic sites. We utilized a combination of low-temperature IR spectroscopy, 2D NMR spectroscopy, nano-MS (ESI) investigations, as well as density functional theory computations [M06/6-31+ G (d, p), including solvent corrections as well ...