1861-02-5Relevant articles and documents
STEREOISOTOPIC STUDY OF THE REDUCTION OF 1-PHENYLETHANOL BY ETHERATED BORON TRIFLUORIDE-TRIETHYLSILANE SYSTEM
Smonou, Ioulia,Orfanopoulos, Michael
, p. 5793 - 5796 (1988)
The kinetic hydrogen-deuterium isotope effects and the stereochemistry of the deoxygenation of 1-phenylethanol with boron trifluoride and triethylsilane have been studied.The results are consistent with a mechanism that involves of the formation of the phenethyl cation in a rate determining step and its fast reduction with triethylsilane.
Room-Temperature Palladium-Catalyzed Deuterogenolysis of Carbon Oxygen Bonds towards Deuterated Pharmaceuticals
Ou, Wei,Xiang, Xudong,Zou, Ru,Xu, Qing,Loh, Kian Ping,Su, Chenliang
supporting information, p. 6357 - 6361 (2021/02/16)
Site-specific incorporation of deuterium into drug molecules to study and improve their biological properties is crucial for drug discovery and development. Herein, we describe a palladium-catalyzed room-temperature deuterogenolysis of carbon–oxygen bonds
Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration
Wang, Yong,Cao, Xinyi,Zhao, Leyao,Pi, Chao,Ji, Jingfei,Cui, Xiuling,Wu, Yangjie
supporting information, p. 4119 - 4129 (2020/08/10)
A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).
Optically Active 1-Deuterio-1-phenylethane – Preparation and Proof of Enantiopurity
Küppers, Julian,Rabus, Ralf,Wilkes, Heinz,Christoffers, Jens
, p. 2629 - 2634 (2019/03/28)
Enantiopure (S)-(1-2H)ethylbenzene was prepared in two steps from optically active (S)-1-phenylethanol via (R)-(1-chloroethyl)benzene (two inversions of configuration). Since the value for the specific rotation [α] is very low for the enantiomers of (1-2H)ethylbenzene, the enantiopurity of the synthetic product could not be determined with certainty by polarimetry. Therefore, bis-sulfonamides were prepared by twofold chlorosulfonation (para and ortho) of (S)-(1-2H)ethylbenzene and subsequent amidation with (R)- and (S)-α-phenethylamine. For both diastereoisomers, the (R,R,S)- and the (S,S,S)-sulfonamides, 92 % de was determined by 1H NMR spectroscopy. Therefore, it could be concluded, that (S)-(1-2H)ethylbenzene had been obtained with 92 % ee.