Synthesis 2016; 48(05): 677-686
DOI: 10.1055/s-0035-1561061
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© Georg Thieme Verlag Stuttgart · New York

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

Barbara Bernardim
a  Instituto de Química de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos, SP, Brazil   Email: antonio@iqsc.usp.br
,
Erica D. Couch
b  Department 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
b  Department 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*
a  Instituto de Química de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos, SP, Brazil   Email: antonio@iqsc.usp.br
,
Anita E. Mattson*
b  Department of Chemistry and Biochemistry, The Ohio State University, 100 W. 18th Ave., Columbus, OH 43210, USA   Email: mattson@chemistry.ohio-state.edu
› Author Affiliations
Further Information

Publication History

Received: 24 September 2015

Accepted after revision: 20 November 2015

Publication Date:
11 January 2016 (online)


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.

Supporting Information

 
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