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

Barbara Bernardim; Erica D. Couch; Andrea M. Hardman-Baldwin; Antonio C. B. Burtoloso; Anita E. Mattson

doi:10.1055/s-0035-1561061

Synthesis, Table of Contents

Synthesis 2016; 48(05): 677-686
DOI: 10.1055/s-0035-1561061

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

Barbara Bernardim

^aInstituto de Química de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos, SP, Brazil Email: antonio@iqsc.usp.br

,

Erica D. Couch

^bDepartment of Chemistry and Biochemistry, The Ohio State University, 100 W. 18th Ave., Columbus, OH 43210, USA Email: mattson@chemistry.ohio-state.edu

,

Andrea M. Hardman-Baldwin

^bDepartment of Chemistry and Biochemistry, The Ohio State University, 100 W. 18th Ave., Columbus, OH 43210, USA Email: mattson@chemistry.ohio-state.edu

,

Antonio C. B. Burtoloso*

^aInstituto de Química de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos, SP, Brazil Email: antonio@iqsc.usp.br

,

Anita E. Mattson*

^bDepartment of Chemistry and Biochemistry, The Ohio State University, 100 W. 18th Ave., Columbus, OH 43210, USA Email: mattson@chemistry.ohio-state.edu

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Abstract

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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.

Key words

diazo compounds - substituent effects - homogeneous catalysis - insertion reactions - urea catalysts - phosphate catalysts

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References

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