000134879 001__ 134879
000134879 005__ 20260217205505.0
000134879 0247_ $$2doi$$a10.1002/ejoc.202400146
000134879 0248_ $$2sideral$$a138434
000134879 037__ $$aART-2024-138434
000134879 041__ $$aeng
000134879 100__ $$aSáez, Javier
000134879 245__ $$aSynthesis of ß-Aryl-a,ß-Dehydroaminophosphonates by Pd-Catalyzed Fujiwara–Moritani C-C Coupling
000134879 260__ $$c2024
000134879 5060_ $$aAccess copy available to the general public$$fUnrestricted
000134879 5203_ $$aThe treatment of diethyl α,β‐dehydroaminophosphonate 1 with various arenes (ArH=toluene 2 a, benzene 2 b, anisole 2 c, bromobenzene 2 d, chlorobenzene 2 e, benzyl alcohol 2 f, p‐xylene 2 g) in acetic acid (AcOH) at 120 °C for 8 h in the presence of Pd(OAc)2 (10 % mol, OAc=acetate) and AgOAc (3.4 equivalents) results in the formation of the corresponding β‐aryl derivatives E‐Ar(H)C=C(NHAc)P(O)(OEt)2 3 a–3 g. The reaction proceeds through double C−H activation (arene and alkene) and subsequent C−C oxidative coupling (Fujiwara–Moritani reaction), processes catalyzed by Pd and assisted by Ag. The obtained products 3 a–3 g are isosteric analogs of phenylalanine and are obtained with high selectivity. Thus, geometrical E‐isomers have been obtained in all studied cases, however mixtures of ortho‐/meta‐/para‐isomers are observed when the activated position in the starting arene 2 is considered.
000134879 536__ $$9info:eu-repo/grantAgreement/ES/AEI/PID2019-106394GB-I00$$9info:eu-repo/grantAgreement/ES/DGA/E07-23R$$9info:eu-repo/grantAgreement/ES/DGA/E17-23R$$9info:eu-repo/grantAgreement/ES/MCIN/AEI/10.13039/501100011033$$9info:eu-repo/grantAgreement/ES/MICINN/PID2019-106394GB-I00
000134879 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc-nd$$uhttps://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
000134879 590__ $$a2.7$$b2024
000134879 592__ $$a0.558$$b2024
000134879 591__ $$aCHEMISTRY, ORGANIC$$b16 / 57 = 0.281$$c2024$$dQ2$$eT1
000134879 593__ $$aPhysical and Theoretical Chemistry$$c2024$$dQ2
000134879 593__ $$aOrganic Chemistry$$c2024$$dQ2
000134879 594__ $$a4.3$$b2024
000134879 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000134879 700__ $$aDalmau, David
000134879 700__ $$0(orcid)0000-0001-5652-5170$$aSayago, Francisco J.$$uUniversidad de Zaragoza
000134879 700__ $$0(orcid)0000-0001-9779-5820$$aUrriolabeitia, Esteban P.
000134879 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000134879 773__ $$g27, 18 (2024), e202400146 [6 p.]$$pEUR J ORG CHEM$$tEuropean Journal of Organic Chemistry$$x1434-193X
000134879 8564_ $$s1606917$$uhttps://zaguan.unizar.es/record/134879/files/texto_completo.pdf$$yVersión publicada
000134879 8564_ $$s2767665$$uhttps://zaguan.unizar.es/record/134879/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000134879 909CO $$ooai:zaguan.unizar.es:134879$$particulos$$pdriver
000134879 951__ $$a2026-02-17-20:23:17
000134879 980__ $$aARTICLE