Stable N-heterocyclic carbene (NHC)-palladium(0) complexes as active catalysts for olefin cyclopropanation reactions with ethyl diazoacetate

Martín, Carmen; Molina, Francisco; Álvarez, Eleuterio; Rodríguez Belderraín, Tomás

doi:10.1002/chem.201102900

Author

Martín, Carmen; Molina, Francisco; Álvarez, Eleuterio; Rodríguez Belderraín, Tomás
Publication Date

2011
Publisher

Wiley-VCH Verlag
Citation

Martín, C., Molina, F., Álvarez, E., Rodríguez Belderraín, T.: "Stable N-heterocyclic carbene (NHC)-palladium(0) complexes as active catalysts for olefin cyclopropanation reactions with ethyl diazoacetate". Chemistry - A European Journal. Vol. 17, n. 52, págs. 14885–14895, (2011). DOI: 10.1002/chem.201102900
Abstract

The Pd(0) complexes NHCPdLn (NHC = N-heterocyclic carbene ligand; L = styrene for n = 2 or PR3 for n = 1) efficiently catalyze the olefin cyclopropanation using ethyl diazoacetate (EDA) as the carbene source with activities that improve any other previous described catalytic system based on this metal. Mechanistic studies have shown that all those catalyst precursors deliver in solution the same catalytic species (IPr)Pd(sty), a 14e, unsaturated intermediate that further reacts with EDA to afford (IPr)Pd(=CHCO2Et)(sty), from which cyclopropane is formed.
URI

http://hdl.handle.net/10272/11567
Project

info:eu-repo/grantAgreement/Ministerio de Ciencia e Innovacion [CTQ2008-00042BQU, CTQ2011-24502]
info:eu-repo/grantAgreement/Junta de Andalucia [P07-FQM-02794]

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Stable N-heterocyclic carbene (NHC)-palladium(0) complexes as active catalysts for olefin cyclopropanation reactions with ethyl diazoacetate

Author

Martín, Carmen; Molina, Francisco; Álvarez, Eleuterio; Rodríguez Belderraín, Tomás UHU Authority

Publication Date

2011

Publisher

Wiley-VCH Verlag

Citation

Martín, C., Molina, F., Álvarez, E., Rodríguez Belderraín, T.: "Stable N-heterocyclic carbene (NHC)-palladium(0) complexes as active catalysts for olefin cyclopropanation reactions with ethyl diazoacetate". Chemistry - A European Journal. Vol. 17, n. 52, págs. 14885–14895, (2011). DOI: 10.1002/chem.201102900

Abstract

The Pd(0) complexes NHCPdLn (NHC = N-heterocyclic carbene ligand; L = styrene for n = 2 or PR3 for n = 1) efficiently catalyze the olefin cyclopropanation using ethyl diazoacetate (EDA) as the carbene source with activities that improve any other previous described catalytic system based on this metal. Mechanistic studies have shown that all those catalyst precursors deliver in solution the same catalytic species (IPr)Pd(sty), a 14e, unsaturated intermediate that further reacts with EDA to afford (IPr)Pd(=CHCO2Et)(sty), from which cyclopropane is formed.

URI

http://hdl.handle.net/10272/11567

Project

info:eu-repo/grantAgreement/Ministerio de Ciencia e Innovacion [CTQ2008-00042BQU, CTQ2011-24502]
info:eu-repo/grantAgreement/Junta de Andalucia [P07-FQM-02794]

Fichero	Tamaño	Formato	Ver	Description
Stable_N-heterocyclic.pdf	1.928Mb	PDF	View/Open	versión post-print

Fichero	Tamaño	Formato	Ver	Description
Stable_N-heterocyclic.pdf	1.928Mb	PDF	View/Open	versión post-print