Carbonylative Negishi-Type Coupling of 2-Iodoglycals with Alkyl and Aryl Halides

Author(s)

Esteves, Henrique A. ^[1] ; Darbem, Mariana P. ^[1] ; Pimenta, Daniel C. ^[2] ; Stefani, Helio A. ^[1]

Affiliation

^[1] Univ Sao Paulo, Dept Farm, Fac Ciencias Farmaceut, Av Prof Lineu Prestes 580, BR-05508000 Sao Paulo, SP - Brazil

^[2] Inst Butantan, Av Vital Brasil 1500, BR-05503000 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2019, n. 44, p. 7384-7388, NOV 30 2019.
• Web of Science Citations: 1

Abstract

C-Glycosides are valuable organic compounds in the field of medicinal chemistry due to their ubiquity inside living systems and pronounced biological activity. Herein, we describe an approach to alkyl-ketones bearing glycal units via the Pd-catalyzed carbonylative coupling of 2-iodoglycals and alkyl and aryl halides. Examples bearing a variety of functional groups are presented as well as a mechanistic proposal for this transformation. (AU)

• FAPESP's process: 17/26673-2 - CuH-Catalyzed fluorination of alkenes and PET applications
• Grantee: Carlos Henrique Alves Esteves
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 17/24821-4 - Carbonylative Coupling and Intramolecular Cycloaddition [2 + 2] Reactions Employing D-Glucal
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/24396-9 - Triazolic 2-Aryloxazolines: synthesis of small libraries, biological activity, fluorescence and ligands
• Grantee: Mariana Pompilio Darbem Rocha
• Support Opportunities: Scholarships in Brazil - Doctorate