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      CO Extrusion in Homogeneous Gold Catalysis: Reactivity of Gold Acyl Species Generated through Water Addition to Gold Vinylidenes

      , , , ,
      Angewandte Chemie International Edition
      Wiley-Blackwell

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          Homogeneous Gold Catalysis Beyond Assumptions and Proposals-Characterized Intermediates

          A. Hashmi (2010)
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            Homogene Gold-Katalyse jenseits von Vermutungen und Annahmen - charakterisierte Intermediate

            A. Hashmi (2010)
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              Experimental and computational evidence for gold vinylidenes: generation from terminal alkynes via a bifurcation pathway and facile C-H insertions.

              Facile cycloisomerization of (2-ethynylphenyl)alkynes is proposed to be promoted synergistically by two molecules of BrettPhosAuNTf(2), affording tricyclic indenes in mostly good yields. A gold vinylidene is most likely generated as one of the reaction intermediates on the basis of both mechanistic studies and theoretical calculations. Different from the well-known Rh, Ru, and W counterparts, this novel gold species is highly reactive and undergoes facile intramolecular C(sp(3))-H insertions as well as O-H and N-H insertions. The formation step for the gold vinylidene is predicted theoretically to be complex with a bifurcated reaction pathway. A pyridine N-oxide acts as a weak base to facilitate the formation of an alkynylgold intermediate, and the bulky BrettPhos ligand in the gold catalyst likely plays a role in sterically steering the reaction toward formation of the gold vinylidene. © 2011 American Chemical Society
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                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley-Blackwell
                14337851
                January 26 2015
                January 26 2015
                : 54
                : 5
                : 1666-1670
                Article
                10.1002/anie.201409859
                8eb1b1b1-70ce-4447-b04e-4cfd02a7027b
                © 2015

                http://doi.wiley.com/10.1002/tdm_license_1.1

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