Ytterbium(III)-catalyzed three-component reactions: synthesis of 4-organoselenium-quinolines

Author(s)

de Oliveira, Isadora M. ^[1] ; Vasconcelos, Stanley S. N. ^[2] ; Barbeiro, Cristiane S. ^[2] ; Correra, Thiago C. ^[1] ; Shamim, Anwar ^[1] ; Pimenta, Daniel C. ^[3] ; Caracelli, Ignez ^[4] ; Zukerman-Schpector, Julio ^[5] ; Stefani, Helio A. ^[2] ; Manarin, Flavia ^[6]

Affiliation

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

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

^[3] Inst Butantan, Sao Paulo, SP - Brazil

^[4] Univ Fed Sao Carlos, Dept Fis, Sao Carlos, SP - Brazil

^[5] Univ Fed Sao Carlos, Dept Quim, Sao Carlos, SP - Brazil

^[6] Univ Estadual Oeste Parana, CECE, Toledo, PR - Brazil

• Document type: Journal article
• Source: NEW JOURNAL OF CHEMISTRY; v. 41, n. 18, p. 9884-9888, SEP 21 2017.
• Web of Science Citations: 6

Abstract

4-Organoselenium-quinolines were synthesized via model multi-component Povarov (MCR) reactions between p-anisidine, ethyl glyoxylate and ethynyl(phenyl) selane, catalyzed by the Lewis acid Yb(OTf)(3), with yields ranging from moderate to good. This method is advantageous in that there is no requirement for an oxidant and that the reaction has a wide scope. These 4-organoselenium-quinolines allowed access to 4-alkynyl-quinolines, which were synthesized via copper free Sonogashira cross-coupling reactions catalyzed by a new palladium catalyst that employs an oxazoline derivative as a ligand. A plausible mechanism was proposed based on HRMS studies. (AU)

• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support type: Research Projects - Thematic Grants
• FAPESP's process: 14/15962-5 - Reaction mechanism of asymmetric catalysts by mass spectrometry and gas-phase vibrational ion spectroscopy
• Grantee: Thiago Carita Correra
• Support type: Research Grants - Young Investigators Grants
• FAPESP's process: 13/17960-7 - Functionalization of 3-iodo-(L)-Tyrosine via Suzuki-Miyaura reaction using potassium organotrifluoroborate salts
• Grantee: Stanley Nunes Siqueira Vasconcelos
• Support type: 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 type: Scholarships in Brazil - Doctorate (Direct)