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An Efficient Synthesis of Polysubstituted Pyridines via C sp 3 H Oxidation and CS Cleavage of Dimethyl Sulfoxide
Author(s) -
Wu Xia,
Zhang Jingjing,
Liu Shan,
Gao Qinghe,
Wu Anxin
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500683
Subject(s) - chemistry , dimethyl sulfoxide , formic acid , sulfoxide , pyridine , bond cleavage , catalysis , cleavage (geology) , formate , methylene , substrate (aquarium) , organic chemistry , medicinal chemistry , combinatorial chemistry , geotechnical engineering , fracture (geology) , engineering , oceanography , geology
Abstract An expedient cleavage of the CS bond of dimethyl sulfoxide (DMSO) has been developed for the preparation of substituted pyridines from ketones. In this transformation, the co‐product formic acid was formed from ammonium formate, which acted as an important catalyst for the reaction. Notably, this transformation exhibited a broad substrate scope towards a wide variety of different ketones to give the corresponding substituted pyridines in high yields. Mechanistic studies suggested that dimethyl sulfoxide delivered a methylene fragment, which was subsequently captured in situ to give a pyridine.