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Literature DB >> 22621418

Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

Timothy J Brown¹, Dieter Weber, Michel R Gagné, Ross A Widenhoefer.

Abstract

Mechanistic investigation of gold(I)-catalyzed intramolecular allene hydroalkoxylation established a mechanism involving rapid and reversible C-O bond formation followed by turnover-limiting protodeauration from a mono(gold) vinyl complex. This on-cycle pathway competes with catalyst aggregation and formation of an off-cycle bis(gold) vinyl complex.

Entities: Chemical Disease Species

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Year: 2012 PMID： 22621418 PMCID： PMC3433713 DOI： 10.1021/ja303844h

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

28 in total

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3. Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

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Review 4. Gold and platinum catalysis--a convenient tool for generating molecular complexity.

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5. Heterocycles from gold catalysis.

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6. Gold(I)-Catalyzed Enantioselective Intramolecular Hydroamination of Allenes with Ureas.

Authors: Hao Li; Seong Du Lee; Ross A Widenhoefer
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7. Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds.

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9. Synthesis and structural characterization of stable organogold(I) compounds. Evidence for the mechanism of gold-catalyzed cyclizations.

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6. Enantioselective Tandem Cyclization of Alkyne-Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis.

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