RT Journal Article
T1 A fully recyclable heterogenized Cu catalyst for the general carbene transfer reaction in batch and flow
A1 Maestre Cera, Lourdes
A1 Ozkal, Erhan
A1 Ayats, Carles
A1 Beltrán Martín, Álvaro
A1 Díaz Requejo, María Mar
A1 Pérez Romero, Pedro José
A1 Pericàs, Miquel A.
AB A polystyrene-linked tris(triazolyl)methanecopper(I) cationic catalyst operates under heterogeneousconditions for the reaction of ethyl diazoacetate (EDA) with an array of substrates. Carbon–hydrogen aswell as X–H (X ¼ O, N) functionalization derived from the formal transfer of the carbene moiety(:CHCO2Et) from the copper center and subsequent insertion have been achieved, the reactionspermitting repeated catalyst recycling and reuse. The addition of the same carbene unit to benzeneleading to a cycloheptatriene derivative (B¨uchner reaction) or to phenylacetylene (cyclopropenation)took place at similar rates to the insertion processes and with the same catalyst recyclability. The use ofthis heterogenized cationic Cu catalyst in continuous flow has also been implemented. Keycharacteristics of the flow process are its high and constant turnover frequency (TOF) (residence timesof 1 min still lead to full conversion in the reaction with ethanol after 48 h operation) and its suitabilityfor the sequential performance of different types of carbene transfer reactions with a simple andaffordable experimental setup.
PB Royal Society of Chemistry
SN 2041-6520
SN 2041-6539 (electrónico)
YR 2015
FD 2015
LK http://hdl.handle.net/10272/13530
UL http://hdl.handle.net/10272/13530
LA eng
NO Maestre Cera, L., Ozkal, E., Ayats, C., Beltrán Martín, A., Díaz Requejo, M.M., Pérez Romero, P.J., Pericàs, M.A.: "A fully recyclable heterogenized Cu catalyst for the general carbene transfer reaction in batch and flow". Chemical Science. 1510–1515. Vol. 6, págs. 1510–1515, (2015). DOI: 10.1039/c4sc03277b
NO This work was funded by MINECO (grants CTQ2011-28942-C02-01 and CTQ2012-38594-C02-01), DEC-Generalitat de Catalunya (Grant 2014SGR827), Junta de Andalucia (P10-FQM-06292) and ICIQ Foundation. The ICIQ team also thanks MINECO for support through Severo Ochoa Excellence Accreditation 2014-2018 (SEV-2013-0319). L. M. thanks MECD for a FPU fellowship. E. O. thanks ICIQ for a postdoctoral fellowship. C. A. thanks MINECO for a Juan de la Cierva posdoctoral fellowship.
DS Repositorio Institucional de la Universidad de Huelva
RD 31 may 2026