Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes

Cano Rico, Israel; Álvarez, Eleuterio; Nicasio Jaramillo, María Carmen; Pérez Romero, Pedro José

doi:10.1021/ja109732s

Author

Cano Rico, Israel; Álvarez, Eleuterio; Nicasio Jaramillo, María Carmen; Pérez Romero, Pedro José
Publication Date

2011
Publisher

American Chemical Society
Citation

Cano. I.. Álvarez, E., Nicasio Jaramillo, M.C., Pérez Romero, P.J.: "Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes". Journal of the American Chemical Society. Vol 133, págs. 191-193, (2011). DOI: 10.1021/ja109732s
Abstract

The reaction of 1-alkynes with acylazides in the presence of [Tpm*,BrCu(NCMe)]BF4 (Tpm*,Br = tris(3,5-dimethyl-4-bromopyrazolyl)methane) as the catalyst provides 2,5-oxazoles in moderate to high yields. This is a novel transformation of CuAAC type, that constitutes a significant variation of the commonly observed [3+2] cycloaddition reaction to yield 1,2,3-triazoles
URI

http://hdl.handle.net/10272/11553
Project

info:eu-repo/grantAggreement/MEC [Proyecto CTQ2008-00042/BQU, CSD2006-003]
info:eu-repo/grantAggreement/Junta de Andalucia [Proyecto P07-FQM-02745]

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Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes

Author

Cano Rico, Israel UHU Authority

; Álvarez, Eleuterio; Nicasio Jaramillo, María Carmen UHU Authority

; Pérez Romero, Pedro José UHU Authority

Publication Date

2011

Publisher

American Chemical Society

Citation

Cano. I.. Álvarez, E., Nicasio Jaramillo, M.C., Pérez Romero, P.J.: "Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes". Journal of the American Chemical Society. Vol 133, págs. 191-193, (2011). DOI: 10.1021/ja109732s

Abstract

The reaction of 1-alkynes with acylazides in the presence of [Tpm*,BrCu(NCMe)]BF4 (Tpm*,Br = tris(3,5-dimethyl-4-bromopyrazolyl)methane) as the catalyst provides 2,5-oxazoles in moderate to high yields. This is a novel transformation of CuAAC type, that constitutes a significant variation of the commonly observed [3+2] cycloaddition reaction to yield 1,2,3-triazoles

URI

http://hdl.handle.net/10272/11553

Project

info:eu-repo/grantAggreement/MEC [Proyecto CTQ2008-00042/BQU, CSD2006-003]
info:eu-repo/grantAggreement/Junta de Andalucia [Proyecto P07-FQM-02745]

Fichero	Tamaño	Formato	Ver	Description
Regioselective_formation.pdf	631.4Kb	PDF	View/Open	versión post-print

Fichero	Tamaño	Formato	Ver	Description
Regioselective_formation.pdf	631.4Kb	PDF	View/Open	versión post-print