Visible-Light-Promoted Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides

Author(s)

Echemendia, Radell ; de Oliveira, Kleber T. ; Burtoloso, Antonio C. B.

• Document type: Journal article
• Source: ORGANIC LETTERS; v. 24, n. 35, p. 5-pg., 2022-08-26.

Abstract

A novel visible-light-promoted coupling of diazoketones with sulfoxonium ylides, employing a violet light-emitting diode, is described under both batch and continuous flow conditions. This transformation permits the direct synthesis of synthetically useful 1,3-dicarbonyl sulfoxonium ylides (33 examples, 21-85% yields), by means of an acylation from the in situ and selective generation of ketenes. The reaction performed under flow conditions proved to be very efficient, providing the 1,3-dicarbonyl sulfoxonium ylides with higher yields and shorter reaction times. (AU)

• FAPESP's process: 19/27176-8 - Asymmetric photocatalysis applied to the synthesis of Brivaracetam: synthetic approaches employing enabling technologies for chemical synthesis
• Grantee: Kleber Thiago de Oliveira
• Support Opportunities: Regular Research Grants
• FAPESP's process: 17/23329-9 - Synthesis of substituted cyclopentanes and long chain polyols from abundant chemical platforms derived from biomass
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants
• FAPESP's process: 20/06874-6 - Applications of technologies and synthetic methodologies developed under continuous flow conditions at LQBO-UFSCar for the preparation of molecules with biological activities and APIs
• Grantee: Kleber Thiago de Oliveira
• Support Opportunities: Regular Research Grants
• FAPESP's process: 19/12300-5 - Synthesis of butenolides and butyrolactams from sulfur ylides and diazocompounds
• Grantee: Radell Echemendía Pérez
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 13/07276-1 - CEPOF - Optics and Photonic Research Center
• Grantee: Vanderlei Salvador Bagnato
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 20/07147-0 - Enantioselective alpha-heterofunctionalization of carbonyl compounds using sulfoxonium ylides
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants