A fully recyclable heterogenized Cu catalyst for the general carbene transfer reaction in batch and flow.

Autor:	Maestre L; Laboratorio de Catálisis Homogénea , Unidad Asociada al CSIC , CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química y Ciencia de Materiales , Universidad de Huelva , 21007 Huelva , Spain . Email: perez@dqcm.uhu.es ; Email: mmdiaz@dqcm.uhu.es ; Tel: +34 959 219956., Ozkal E; Institute of Chemical Research of Catalonia (ICIQ) , Avda. Països Catalans 16 , 43007 , Tarragona , Catalonia , Spain . Email: mapericas@iciq.es ; Tel: +34 977 920 243., Ayats C; Institute of Chemical Research of Catalonia (ICIQ) , Avda. Països Catalans 16 , 43007 , Tarragona , Catalonia , Spain . Email: mapericas@iciq.es ; Tel: +34 977 920 243., Beltrán Á; Laboratorio de Catálisis Homogénea , Unidad Asociada al CSIC , CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química y Ciencia de Materiales , Universidad de Huelva , 21007 Huelva , Spain . Email: perez@dqcm.uhu.es ; Email: mmdiaz@dqcm.uhu.es ; Tel: +34 959 219956., Díaz-Requejo MM; Laboratorio de Catálisis Homogénea , Unidad Asociada al CSIC , CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química y Ciencia de Materiales , Universidad de Huelva , 21007 Huelva , Spain . Email: perez@dqcm.uhu.es ; Email: mmdiaz@dqcm.uhu.es ; Tel: +34 959 219956., Pérez PJ; Laboratorio de Catálisis Homogénea , Unidad Asociada al CSIC , CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química y Ciencia de Materiales , Universidad de Huelva , 21007 Huelva , Spain . Email: perez@dqcm.uhu.es ; Email: mmdiaz@dqcm.uhu.es ; Tel: +34 959 219956., Pericàs MA; Institute of Chemical Research of Catalonia (ICIQ) , Avda. Països Catalans 16 , 43007 , Tarragona , Catalonia , Spain . Email: mapericas@iciq.es ; Tel: +34 977 920 243.; Departament de Química Orgànica , Universitat de Barcelona , 08028 Barcelona , Spain.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2015 Feb 01; Vol. 6 (2), pp. 1510-1515. Date of Electronic Publication: 2014 Nov 28.
DOI:	10.1039/c4sc03277b
Abstrakt:	A polystyrene-linked tris(triazolyl)methanecopper(i) cationic catalyst operates under heterogeneous conditions for the reaction of ethyl diazoacetate (EDA) with an array of substrates. Carbon-hydrogen as well as X-H (X = O, N) functionalization derived from the formal transfer of the carbene moiety (:CHCO 2 Et) from the copper center and subsequent insertion have been achieved, the reactions permitting repeated catalyst recycling and reuse. The addition of the same carbene unit to benzene leading to a cycloheptatriene derivative (Büchner reaction) or to phenylacetylene (cyclopropenation) took place at similar rates to the insertion processes and with the same catalyst recyclability. The use of this heterogenized cationic Cu catalyst in continuous flow has also been implemented. Key characteristics of the flow process are its high and constant turnover frequency (TOF) (residence times of 1 min still lead to full conversion in the reaction with ethanol after 48 h operation) and its suitability for the sequential performance of different types of carbene transfer reactions with a simple and affordable experimental setup.
Databáze:	MEDLINE
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