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Palladium-catalyzed oxidative heterocyclodehydration-alkoxycarbonylation of 3-yne-1,2-diols: a novel and expedient approach to furan-3-carboxylic esters

✍ Scribed by Bartolo Gabriele; Lucia Veltri; Raffaella Mancuso; Pierluigi Plastina; Giuseppe Salerno; Mirco Costa

Book ID
104097386
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
223 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

A novel and convenient approach to furan-3-carboxylic esters 2 is presented, based on palladium-catalyzed direct oxidative carbonylation of readily available 3-yne-1,2-diols 1. The process, corresponding to a sequential combination between a 5-endo-dig heterocyclodehydration step and an oxidative alkoxycarbonylation stage, is catalyzed by PdI 2 in conjunction with an excess of KI under relatively mild conditions (100 °C in ROH under 40 atm of a 4:1 mixture of CO-air).

📜 SIMILAR VOLUMES

A simple and convenient synthesis of sub
A simple and convenient synthesis of substituted furans and pyrroles by CuCl2-catalyzed heterocyclodehydration of 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols
✍ Bartolo Gabriele; Pierluigi Plastina; Mabel V. Vetere; Lucia Veltri; Raffaella M 📂 Article 📅 2010 🏛 Elsevier Science 🌐 French ⚖ 229 KB

A simple and economical synthesis of substituted furans and pyrroles, by ligand-free CuCl 2 -catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and N-Boc-or N-tosyl-1-amino-3-yn-2-ols, respectively, is presented. Reactions are carried out in MeOH at 80-100 °C for 1-24 h and afford

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A General and Expedient Synthesis of 5- and 6-Membered Cyclic Carbonates by Palladium-Catalyzed Oxidative Carbonylation of 1,2- and 1,3-Diols
✍ Prof. Dr. Bartolo Gabriele; Dr. Raffaella Mancuso; Prof. Giuseppe Salerno; Dr. L 📂 Article 📅 2011 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 413 KB

## Abstract 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 °C in __N__,__N__‐dimethylacetamide as the solvent under 20 atm (a