Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides

Alvarez-Perez, A. ; Esteruelas, M.A. ; Izquierdo, S. ; Varela, J.A. ; Saa, C.

Resumen: 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(eta(2)-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.

Idioma: Inglés

DOI: 10.1021/acs.orglett.9b01993

Año: 2019

Publicado en: ORGANIC LETTERS 21, 13 (2019), 5346-5350
ISSN: 1523-7060

Factor impacto JCR: 6.091 (2019)

Categ. JCR: CHEMISTRY, ORGANIC rank: 4 / 57 = 0.07 (2019) - Q1 - T1

Factor impacto SCIMAGO: 2.032 - Biochemistry (Q1) - Physical and Theoretical Chemistry (Q1) - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E06-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2014-59015-R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-82935-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-87939-R

Tipo y forma: Article (PostPrint)