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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

alpha-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

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Caiuby, Clarice A. D. [1] ; de Jesus, Matheus P. [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 3
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Organic Chemistry; v. 85, n. 11, p. 7433-7445, JUN 5 2020.
Web of Science Citations: 0

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate alpha-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by {[}Ir(cod)Cl](2) (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding beta-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield). (AU)

FAPESP's process: 09/54040-8 - Acquisition of a high-resolution Orbitrap mass spectrometer for the discovery and structural analysis of biologically active compounds: applications in proteomics, biomarkers, synthesis, isolation, and characterization of natural products, studies of redox systems in food and enzymatic synthesis
Grantee:Emanuel Carrilho
Support Opportunities: Multi-user Equipment Program
FAPESP's process: 13/50228-8 - Biodiversity components, and their metabolic characters, of Brazilian Islands: an integrated approach
Grantee:Roberto Gomes de Souza Berlinck
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 17/23837-4 - Exploring the application of diazocarbonyl compounds and sulfur ylides in the asymmetric ring opening reactions with epoxides for the synthesis of oxetanes and functionalized alcohols
Grantee:Clarice Alves Dale Caiuby
Support Opportunities: Scholarships in Brazil - Doctorate
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