A General and Expedient Synthesis of 5-and 6-Membered Cyclic Carbonates by Palladium-Catalyzed Oxidative Carbonylation of 1,2-and 1,3-Diols

被引：51

作者：

Gabriele, Bartolo ^{[1
]}

Mancuso, Raffaella ^{[2
]}

Salerno, Giuseppe ^{[2
]}

Veltri, Lucia ^{[2
]}

Costa, Mirco ^{[3
]}

Dibenedetto, Angela ^{[4
]}

机构：

[1] Univ Calabria, Dipartimento Sci Farmaceut, I-87036 Arcavacata Di Rende, CS, Italy

[2] Univ Calabria, Dipartimento Chim, I-87036 Arcavacata Di Rende, CS, Italy

[3] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

[4] Univ Bari, Dipartimento Chim, I-70126 Bari, Italy

来源：

CHEMSUSCHEM | 2011年 / 4卷 / 12期

关键词：

carbonylation; catalysis; industrial chemistry; diols; palladium; GLYCEROL CARBONATE; DIMETHYL CARBONATE; TETRAHYDROFURAN DERIVATIVES; 1,2-GLYCEROL CARBONATE; VERSATILE SYNTHESIS; ORGANIC CARBONATES; CHEMICAL FIXATION; CASCADE REACTIONS; EFFICIENT METHOD; DIOXIDE;

D O I：

10.1002/cssc.201100250

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present a general, practical, and efficient approach to 5- and 6-membered organic carbonates by palladium-catalyzed direct oxidative carbonylation of 1,2- and 1,3-diols, respectively. Reactions were carried out at 100 degrees C in N,N-dimethylacetamide as the solvent under 20 atm (at 25 degrees C; 1 atm=101.3 kPa) of a 4:1 v/v CO/air mixture in the presence of 0.52 mol% of PdI2 and KI (KI/PdI2 molar ratio=10). Excess dehydrating agent, such as trimethyl orthoacetate, was necessary in several cases to obtain appreciable results. The method could also be applied to the synthesis of a high-value-added glycerol carbonate from glycerol, a readily available raw material. When applied to a-D-glucose, a double carbonylation process took place, with direct formation of a-D-glucofuranose 1,2:5,6-dicarbonate.

引用

页码：1778 / 1786

页数：9

共 102 条

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