112498-18-7Relevant academic research and scientific papers
Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes
Fu, Yiwei,Li, Hao,Liu, Yonghai,Mang, Zhiguo,Shi, Lei,Sun, Chengyu,Yu, Yang
supporting information, p. 8127 - 8131 (2020/11/03)
We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.
LIGAND COUPLING AND PSEUDOROTATION IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENTS
Oae, Shigeru,Takeda, Takashi,Kawai, Tsutomu,Furukawa, Naomichi
, p. 133 - 138 (2007/10/02)
In the reaction of benzyl 2-pyridyl sulfoxide (1) with C6H5CH2MgCl, the incoming Grignard reagent tends to couple preferentially with 2-pyridyl group at lower temperatures, whereas, at higher temperatures, coupling between benzyl and 2-pyridyl groups with 1 tends to increase due presumably to the relatively more facile pseudorotation at higher temperatures.
Ligand Coupling within ?-Sulphurane Intermediates formed in the Reaction of Benzyl 2-Pyridyl and Related Sulphoxides with Grignard reagents
Oae, Shigeru,Kawai, Tsutomu,Furukawa, Naomichi,Iwasaki, Fujiko
, p. 405 - 412 (2007/10/02)
The reaction of benzyl or 1-phenylethyl 2-pyridyl sulphoxide (1) or (18) with a Grignard reagent was found to give the ligand-coupling product, i.e., 2-benzylpyridine or 2-(1-phenylethyl)pyridine (2) or (22) in excellent yield.This coupling reaction was found to proceed whithin the ?-sulphurane formed as an intermediate upon treatment of benzyl 2-pyridyl and related sulphoxides with a Grignard reagent.The stereochemical course of this coupling reaction involves complete retention at the benzylic carbon.
