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Gold-catalyzed hydroarylation of allenes: a highly regioselective carbon-carbon bond formation producing six-membered rings.

Toshiaki Watanabe, +3 more
- 09 Oct 2007 - 
- Vol. 9, Iss: 23, pp 4821-4824
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TLDR
Gold-catalyzed intramolecular hydroarylation of allenic anilines and phenols offers an efficient route to dihydroquinoline and chromene derivatives under mild reaction conditions, leading to a highly selective formation of six-membered rings.
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This article is published in Organic Letters.The article was published on 2007-10-09. It has received 110 citations till now. The article focuses on the topics: Carbon–carbon bond.

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Citations
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Ligand effects in homogeneous Au catalysis.

TL;DR: The ways in which selectivity can be controlled in homogeneous Au catalysis are enumerated, in the hope that lessons to guide catalyst selection and the design of new catalysts may be distilled from a thorough evaluation of ligand, counterion, and oxidation state effects as they influence chemo-, regio-, and stereoselectivity in homogeneity AuCatalysis.
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Gold-catalyzed organic transformations.

TL;DR: Thanks to gold-based catalysts, various organic transformations have been accessible under facile conditions with both high yields and chemoselectivity.
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Alternative synthetic methods through new developments in catalysis by gold.

TL;DR: The results show clear trends in gold-Catalyzed C-H Bond Functionalization and Selective Reductions, and catalytic Hydrogenation of Alkenes and 1,3-Dienes, as well as in other areas of science.
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Coinage Metal-Assisted Synthesis of Heterocycles

TL;DR: The chiral stationary phase for Heterocycloaddition showed good chiral recognition ability towards various racemates, including N/O-Vinylation/Arylation and Radical Cyclization of Haloalkenes and Haloalkynes.
References
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Journal ArticleDOI

Relativistic effects in homogeneous gold catalysis

TL;DR: This Review draws on experimental and computational data to present the current understanding of homogeneous gold catalysis, focusing on previously unexplored reactivity and its application to the development of new methodology.
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Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans

TL;DR: In this paper, a solid-phase synthesis of the benzopyran motif is developed employing a unique cycloloading strategy that relies on the use of a new, polystyrene-based selenenyl bromide resin.
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Intramolecular [4 + 2] cycloadditions of 1,3-enynes or arylalkynes with alkenes with highly reactive cationic phosphine Au(I) complexes.

TL;DR: New Au(I) complexes with bulky, biphenyl phosphines are the most reactive catalysts for the cyclizations of enynes with an aryl ring at the alkyne.
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Highly Active Au(I) Catalyst for the Intramolecular exo-Hydrofunctionalization of Allenes with Carbon, Nitrogen, and Oxygen Nucleophiles

TL;DR: A Au(I)-catalyzed intramolecular hydroamination of N-allenyl carbamates tolerated substitution at the alkyl and allenyl carbon atoms and was effective for the formation of piperidine derivatives and the corresponding oxygen heterocycles in good yield with high exo-selectivity.
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1,2-Halogen Migration in Haloallenyl Ketones: Regiodivergent Synthesis of Halofurans

TL;DR: It was found that, depending on the nature of the Au catalyst used, either selective bromine migration or hydrogen shift occurs, leading to the formation of 3- or 2-bromofurans, respectively, in haloallenyl ketones.
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