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Dimethyl Sulfoxide as an Oxygen Atom Source Enabled Tandem Conversion of 2‐Alkynyl Carbonyls to 1,2‐Dicarbonyls
Author(s) -
Lu Yuan,
Luo MuJia,
Hu Ming,
Li Yang,
Li JinHeng
Publication year - 2020
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.202000066
Subject(s) - chemistry , tandem , nucleophile , oxygen atom , medicinal chemistry , dimethyl sulfoxide , nucleophilic addition , cleavage (geology) , oxygen , photochemistry , bond cleavage , combinatorial chemistry , molecule , catalysis , organic chemistry , materials science , geotechnical engineering , fracture (geology) , engineering , composite material
A tandem transformation of 2‐alkynyl carbonyl compounds by means of a CuBr 2 /I 2 /DMSO/water system is developed, enabling the fromation of various functionalized 1,2‐dicarbonyl compounds, including 1,2‐diketones, α ‐keto amides and α‐keto ester. This Cu‐promoted iodine‐mediated tandem procedure employs DMSO as the oxygen atom source of the formed carbonyl group through iodonium ion formation, nucleophilic DMSO addition and C−C bond cleavage cascades.