000117352 001__ 117352
000117352 005__ 20230622083326.0
000117352 0247_ $$2doi$$a10.1002/chem.202101414
000117352 0248_ $$2sideral$$a126859
000117352 037__ $$aART-2021-126859
000117352 041__ $$aeng
000117352 100__ $$0(orcid)0000-0001-7904-2729$$aAzpíroz R.
000117352 245__ $$aPreparation of Butadienylpyridines by Iridium-NHC-Catalyzed Alkyne Hydroalkenylation and Quinolizine Rearrangement
000117352 260__ $$c2021
000117352 5060_ $$aAccess copy available to the general public$$fUnrestricted
000117352 5203_ $$aIridium(I) N-heterocyclic carbene complexes of formula Ir(¿2O, O’-BHetA)(IPr)(¿2-coe) [BHetA=bis-heteroatomic acidato, acetylacetonate or acetate; IPr=1, 3-bis(2, 6-diisopropylphenyl)imidazolin-2-carbene; coe=cyclooctene] have been prepared by treating Ir(¿2O, O’-BHetA)(¿2-coe)2 complexes with IPr. These complexes react with 2-vinylpyridine to afford the hydrido-iridium(III)-alkenyl cyclometalated derivatives IrH(¿2O, O’-BHetA)(¿2N, C-C7H6N)(IPr) through the iridium(I) intermediate Ir(¿2O, O’-BHetA)(IPr)(¿2-C7H7N). The cyclometalated IrH(¿2O, O’-acac)(¿2N, C–C7H6N)(IPr) complex efficiently catalyzes the hydroalkenylation of aromatic and aliphatic terminal alkynes and enynes with 2-vinylpyridine to afford 2-(4R-butadienyl)pyridines with Z, E configuration as the major reaction products (yield up to 89 %). In addition, unprecedented (Z)-2-butadienyl-5R-pyridine derivatives have been obtained as minor reaction products (yield up to 21 %) from the elusive 1Z, 3gem-butadienyl hydroalkenylation products. These compounds undergo a thermal 6p-electrocyclization to afford bicyclic 4H-quinolizine derivatives that, under catalytic reaction conditions, tautomerize to 6H-quinolizine to afford the (Z)-2-(butadienyl)-5R-pyridine by a retro-electrocyclization reaction. © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH
000117352 536__ $$9info:eu-repo/grantAgreement/ES/MICINN-FEDER/PID2019-103965GB-I00$$9info:eu-repo/grantAgreement/ES/DGA-FSE/E42-20R
000117352 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc-nd$$uhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
000117352 590__ $$a5.02$$b2021
000117352 592__ $$a1.343$$b2021
000117352 594__ $$a9.1$$b2021
000117352 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b64 / 180 = 0.356$$c2021$$dQ2$$eT2
000117352 593__ $$aChemistry (miscellaneous)$$c2021$$dQ1
000117352 593__ $$aCatalysis$$c2021$$dQ1
000117352 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000117352 700__ $$aGreger I.
000117352 700__ $$0(orcid)0000-0001-7154-7239$$aOro L.A.$$uUniversidad de Zaragoza
000117352 700__ $$0(orcid)0000-0002-1735-6439$$aPassarelli V.$$uUniversidad de Zaragoza
000117352 700__ $$0(orcid)0000-0003-4460-8678$$aCastarlenas R.
000117352 700__ $$0(orcid)0000-0002-3327-0918$$aPérez-Torrente J.J.$$uUniversidad de Zaragoza
000117352 7102_ $$12010$$2760$$aUniversidad de Zaragoza$$bDpto. Química Inorgánica$$cÁrea Química Inorgánica
000117352 773__ $$g27, 46 (2021), 11868-11878$$pChemistry (Weinh.)$$tChemistry - A European Journal$$x0947-6539
000117352 8564_ $$s4431920$$uhttps://zaguan.unizar.es/record/117352/files/texto_completo.pdf$$yVersión publicada
000117352 8564_ $$s2316921$$uhttps://zaguan.unizar.es/record/117352/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000117352 909CO $$ooai:zaguan.unizar.es:117352$$particulos$$pdriver
000117352 951__ $$a2023-06-21-15:03:36
000117352 980__ $$aARTICLE