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Palladium‐Catalyzed Carbonylation of Diols to Cyclic Carbonates
Author(s) -
Pearson David M.,
Conley Nicholas R.,
Waymouth Robert M.
Publication year - 2011
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.201100240
Subject(s) - chemistry , carbonylation , palladium , catalysis , carbon monoxide , medicinal chemistry , sodium acetate , organic chemistry , yield (engineering) , materials science , metallurgy
The catalytic alkoxycarbonylation of 1,2‐diols by (neocuproine)palladium(II) acetate (neocuproine=2,9‐dimethyl‐1,10‐phenanthroline) or palladium(II) acetate/(−)‐sparteine using N ‐chlorosuccinimide as the oxidant affords cyclic carbonates. The oxidative carbonylation of diols proceeds under mild conditions, requiring only 1 atm of carbon monoxide, and produces cyclic carbonates in moderate to good yields. Both 1,2‐ and 1,3‐diols can be carbonylated using (neocuproine)Pd(OAc) 2 and sodium dichloroisocyanuric acid, which serves as a competent oxidant and base for this system, to yield 5‐ and 6‐membered cyclic carbonates.