Palladium-Catalyzed Thio- and Selenocarbonylation of 2-Iodoglycals

Author(s)

Darbem, Mariana P. ^[1] ; Esteves, Henrique A. ^[1] ; de Oliveira, Isadora M. ^[2] ; Pimenta, Daniel C. ^[3] ; Stefani, Helio A. ^[1]

Affiliation

^[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP - Brazil

^[2] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Sao Paulo, SP - Brazil

^[3] Inst Butantan, Av Vital Brasil 1500, BR-05508000 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: CHEMCATCHEM; v. 12, n. 2 NOV 2019.
• Web of Science Citations: 0

Abstract

The carbonylative cross-coupling reactions of 2-iodoglycals with thiols and selenols in the presence of molybdenum hexacarbonyl as a solid source of carbon monoxide is described. This methodology permitted the synthesis of 29 C2-glycosides bearing thioester and selenoester functionalities in moderate to excellent yields and high functional group tolerance. Moreover, this communication describes the first catalytic carbonylative coupling reaction of selenols with a carbon electrophile. (AU)

• 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
• FAPESP's process: 16/04289-3 - Synthesis of calcogeno amino acids derivatives and 4-calcogeno quinolines via multicomponent reactions
• Grantee: Isadora Maria de Oliveira
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• 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