Ligand and copper free Sonogashira coupling to achieve 2-alkynyl D-glucal derivatives: regioselective electrophile promoted nucleophilic 5-endo-dig cyclization

Author(s)

Shamim, Anwar ^[1] ; Vasconcelos, Stanley N. S. ^[2] ; Ali, Bakhat ^[2] ; Madureira, Lucas Sousa ^[3] ; Zukerman-Schpector, J. ^[3] ; Stefani, Helio A. ^{[2, 1]}

Affiliation

^[1] Univ Sao Paulo, Inst Quim, Dept Quim, Sao Paulo, SP - Brazil

^[2] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP - Brazil

^[3] Univ Fed Sao Carlos, Dept Quim, Lab Cristalog Estereodinam & Modelagem Mol, BR-13560 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: Tetrahedron Letters; v. 56, n. 43, p. 5836-5842, OCT 21 2015.
• Web of Science Citations: 12

Abstract

A general approach for the synthesis of 2-alkynyl-D-glucal derivatives has been achieved through a ligand and copper-free Sonogashira coupling of 2-iodo-3,4,6-tri-O-acetyl-D-glucal and terminal alkynes using palladium acetate in DMF at room temperature with very good to excellent yields. The scope of this reaction is shown by regioselective electrophile promoted nucleophilic (EPN) 5-endo-dig cyclization of these alkynyl-D-glucal derivatives using gold(III) chloride in 1,4-dioxane at reflux. (C) 2015 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants