RT Journal Article
T1 Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
A1 Álvarez Pérez, Andrea
A1 Esteruelas Rodrigo, Miguel Ángel
A1 Izquierdo, Susana
A1 Varela Carrete, Jesús Ángel
A1 Saá Rodríguez, Carlos
K1 Alkynes
K1 Amides
K1 Oxidative Annulation
K1 Ruthenium
AB Complex CpRuCl(PPh3)2 catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that the true catalysts of the processes are the vinylidene cations [CpRu(═C═CHR)(PPh3)2]+ which are oxidized to the Ru(η2-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.
PB American Chemical Society
SN 1523-7060
YR 2019
FD 2019
LK http://hdl.handle.net/10347/23355
UL http://hdl.handle.net/10347/23355
LA eng
NO Álvarez-Pérez, A., Esteruelas, M. A., Izquierdo, S., Varela, J. A., Saá, C. (2019). Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides. Org. Lett., 21, 13, 5346-5350
NO NOTICE: This is the peer reviewed version of the following article: Álvarez-Pérez, A., Esteruelas, M. A., Izquierdo, S., Varela, J. A., Saá, C. (2019). Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides. Org. Lett., 21, 13, 5346-5350. [doi: 10.1021/acs.orglett.9b01993]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving
NO This work has received financial support from MINECO (projects CTQ2014-59015R, CTQ2017-87939R, CTQ2017-82935-P and ORFEO-CINQA network CTQ2016-81797-REDC), the Xunta de Ga-licia (project GRC2014/032, ED431C 2018/04, Centro singular de in-vestigación de Galicia accreditation 2016–2019, ED431G/09), DGA (No.E06_17R) and the European Union (European Regional Develop-ment Fund - ERDF). A. A.-P. thanks Spanish MICINN for a predoctoral FPI fellowship
DS Minerva
RD 24 abr 2026