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Iridium(I)\u2010cyclooctadiene complexes having a NHC ligand with a O\u2010 or N\u2010functionalised wingtip efficiently catalysed the oxidation and \u03b2\u2010alkylation of secondary alcohols with primary alcohols in the presence of a base. The cationic complex [Ir(NCCH<jats:sub>3<\/jats:sub>)(cod)(MeIm(2\u2010 methoxybenzyl))][BF<jats:sub>4<\/jats:sub>] (cod=1,5\u2010cyclooctadiene, MeIm=1\u2010methylimidazolyl) having a rigid O\u2010functionalised wingtip, shows the best catalyst performance in the dehydrogenation of benzyl alcohol in acetone, with an initial turnover frequency (TOF<jats:sub>0<\/jats:sub>) of 1283\u2005h<jats:sup>\u22121<\/jats:sup>, and also in the \u03b2\u2010alkylation of 2\u2010propanol with butan\u20101\u2010ol, which gives a conversion of 94\u2009% in 10\u2005h with a selectivity of 99\u2009% for heptan\u20102\u2010ol. We have investigated the full reaction mechanism including the dehydrogenation, the cross\u2010aldol condensation and the hydrogenation step by DFT calculations. Interestingly, these studies revealed the participation of the iridium catalyst in the key step leading to the formation of the new C\uf8ffC bond that involves the reaction of an O\u2010bound enolate generated in the basic medium with the electrophilic aldehyde.<\/jats:p>","DOI":"10.1002\/chem.201502910","type":"journal-article","created":{"date-parts":[[2015,10,24]],"date-time":"2015-10-24T08:57:02Z","timestamp":1445677022000},"page":"17877-17889","source":"Crossref","is-referenced-by-count":114,"title":["Oxidation and \u03b2\u2010Alkylation of Alcohols Catalysed by Iridium(I) Complexes with Functionalised N\u2010Heterocyclic Carbene Ligands"],"prefix":"10.1002","volume":"21","author":[{"given":"M. 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