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      Regioselective Synthesis of Functionalized PyrrolesviaGold(I)-Catalyzed [3+2] Cycloaddition of Stabilized Vinyl Diazo Derivatives and Nitriles

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      Advanced Synthesis & Catalysis
      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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              A bonding model for gold(I) carbene complexes

              The last decade has witnessed dramatic growth in the number of reactions catalyzed by electrophilic gold complexes. While proposed mechanisms often invoke the intermediacy of gold-stabilized cationic species, the nature of bonding in these intermediates remains unclear. Herein, we propose that the carbon-gold bond in these intermediates is comprised of varying degrees of both σ and π-bonding; however, the overall bond order is generally less than or equal to unity. The bonding in a given gold-stabilized intermediate, and the position of this intermediate on a continuum ranging from gold-stabilized singlet carbene to gold-coordinated carbocation, is dictated by the carbene substituents and the ancillary ligand. Experiments show that the correlation between bonding and reactivity is reflected in the yield of gold-catalyzed cyclopropanation reactions.
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                Author and article information

                Journal
                Advanced Synthesis & Catalysis
                Adv. Synth. Catal.
                Wiley-Blackwell
                16154150
                July 08 2013
                July 08 2013
                : 355
                : 10
                : 1948-1954
                Article
                10.1002/adsc.201300346
                3643a722-7633-44d4-af72-eaa15d29f095
                © 2013

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

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