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α‐Csp 3 ‐H Methylenation of Diketones to Synthesize Methylene‐Bridged Bis‐1,3‐Dicarbonyl Compounds and Polysubstituted Pyridines Using the DMSO/Selectfluor System
Author(s) -
Gao Yejun,
Zhou Dongheng,
Ma Yongmin
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801996
Subject(s) - selectfluor , chemistry , methylene , annulation , catalysis , dimethyl sulfoxide , salt (chemistry) , organic chemistry , medicinal chemistry , ammonium
A direct α‐Csp 3 ‐H methylenation of 1,3‐diketones to afford methylene‐bridged bis‐1,3‐dicarbonyl derivatives using dimethyl sulfoxide (DMSO) as a one‐carbon source was achieved in moderate to high yields in the presence of Selectfluor. The 1,3‐diketones can also be efficiently converted into Hantzsch‐type pyridines via one‐pot three‐component annulation reaction in the presence of DMSO and ammonium salt. The procedure avoids the use of transition metal catalysts and the reaction is efficient and operationally convenient.