Divergent Roles of Urea and Phosphoric Acid Derived Catalysts in Reactions of Diazo Compounds

Author(s)

Bernardim, Barbara ^[1] ; Couch, Erica D. ^[2] ; Hardman-Baldwin, Andrea M. ^[2] ; Burtoloso, Antonio C. B. ^[1] ; Mattson, Anita E. ^[2]

Affiliation

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[2] Ohio State Univ, Dept Chem & Biochem, 100 W 18th Ave, Columbus, OH 43210 - USA

• Document type: Journal article
• Source: SYNTHESIS-STUTTGART; v. 48, n. 5, p. 677-686, MAR 2016.
• Web of Science Citations: 11

Abstract

Hydrogen-bond-donor catalysts enable a variety of formal insertion reactions of diazo compounds. The role of the catalyst in the reaction system may vary depending on several factors, including the nucleophilicity of the diazo compound and the acidity of the insertion partner. Ureas and phosphoric acid derivatives can offer complementary reactivity patterns when selected as catalysts for selected O-H and S-H insertion reactions of aryl- and diazo-substituted esters. (AU)

• FAPESP's process: 13/50312-9 - Organocatalytic insertion reactions for drug discovery
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
• Grantee: Carlos Alberto Montanari
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 12/22274-2 - Study in the photochemical Wolff rearrangement from a,b-unsaturated diazoketones. Aplication in diversity synthesis of nitrogen and oxygen heterocycles
• Grantee: Barbara Bernardim de Souza
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 13/25504-1 - Development of new methodologies for the asymmetric a-functionalization of carbonyl compounds using chiral catalysts
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants