000169434 001__ 169434 000169434 005__ 20260227133540.0 000169434 0247_ $$2doi$$a10.1021/acs.orglett.9b01993 000169434 0248_ $$2sideral$$a113166 000169434 037__ $$aART-2019-113166 000169434 041__ $$aeng 000169434 100__ $$aAlvarez-Perez, A. 000169434 245__ $$aRuthenium-Catalyzed Oxidative Amidation of Alkynes to Amides 000169434 260__ $$c2019 000169434 5060_ $$aAccess copy available to the general public$$fUnrestricted 000169434 5203_ $$aComplex 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. 000169434 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E06-17R$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2014-59015-R$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-82935-P$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-87939-R 000169434 540__ $$9info:eu-repo/semantics/openAccess$$aAll rights reserved$$uhttp://www.europeana.eu/rights/rr-f/ 000169434 590__ $$a6.091$$b2019 000169434 591__ $$aCHEMISTRY, ORGANIC$$b4 / 57 = 0.07$$c2019$$dQ1$$eT1 000169434 592__ $$a2.032$$b2019 000169434 593__ $$aBiochemistry$$c2019$$dQ1 000169434 593__ $$aPhysical and Theoretical Chemistry$$c2019$$dQ1 000169434 593__ $$aOrganic Chemistry$$c2019$$dQ1 000169434 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/acceptedVersion 000169434 700__ $$0(orcid)0000-0002-4829-7590$$aEsteruelas, M.A. 000169434 700__ $$0(orcid)0000-0002-6608-1910$$aIzquierdo, S. 000169434 700__ $$aVarela, J.A. 000169434 700__ $$aSaa, C. 000169434 773__ $$g21, 13 (2019), 5346-5350$$pOrg. lett.$$tORGANIC LETTERS$$x1523-7060 000169434 8564_ $$s304258$$uhttps://zaguan.unizar.es/record/169434/files/texto_completo.pdf$$yPostprint 000169434 8564_ $$s2571894$$uhttps://zaguan.unizar.es/record/169434/files/texto_completo.jpg?subformat=icon$$xicon$$yPostprint 000169434 909CO $$ooai:zaguan.unizar.es:169434$$particulos$$pdriver 000169434 951__ $$a2026-02-27-12:35:34 000169434 980__ $$aARTICLE