Literature DB >> 18461941

Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity.

Yuanzhi Xia1, Alexander S Dudnik, Vladimir Gevorgyan, Yahong Li.   

Abstract

Through computational and experimental studies, the mechanisms of gold-catalyzed cycloisomerization of bromoallenyl ketones in toluene have been elucidated. The divergent 1,2-migrations for the Au(I)- and Au(III)-catalyzed reactions have been investigated, and the results confirmed that the regiochemistry is ligand-dependent in cases of Au(PR3)L (L = Cl, OTf, BF4, and SbF6) catalysts.

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Year:  2008        PMID： 18461941      PMCID： PMC2435085          DOI： 10.1021/ja802144t

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


  37 in total

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5.  Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

Authors:  Michael R Luzung; Pablo Mauleón; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-09-21       Impact factor: 15.419

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Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

7.  The reaction mechanism of the hydroamination of alkenes catalyzed by gold(I)-phosphine: the role of the counterion and the N-nucleophile substituents in the proton-transfer step.

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Journal:  J Am Chem Soc       Date:  2008-01-01       Impact factor: 15.419

8.  DFT study of the mechanisms of in water Au(I)-catalyzed tandem [3,3]-rearrangement/Nazarov reaction/[1,2]-hydrogen shift of enynyl acetates: a proton-transport catalysis strategy in the water-catalyzed [1,2]-hydrogen shift.

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Journal:  J Am Chem Soc       Date:  2007-11-21       Impact factor: 15.419

9.  AuCl-catalyzed synthesis of benzyl-protected substituted phenols: a formal [3+3] approach.

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Journal:  Org Lett       Date:  2007-10-03       Impact factor: 6.005

10.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419
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  16 in total

1.  Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

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2.  Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

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Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

3.  Mechanisms for the synthesis of conjugated enynes from diphenylacetylene and trimethylsilylacetylene catalyzed by a nickel(0) complex: DFT study of ligand-controlled selectivity.

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Review 4.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

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Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

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Authors:  Jingna Shao; Rongxing He; Wei Shen; Ming Li
Journal:  J Mol Model       Date:  2014-05-07       Impact factor: 1.810

6.  Solution-phase synthesis of a highly substituted furan library.

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Journal:  ACS Comb Sci       Date:  2012-06-11       Impact factor: 3.784

7.  Mechanism of gold(I)-catalyzed rearrangements of acetylenic amine-N-oxides: computational investigations lead to a new mechanism confirmed by experiment.

Authors:  Elizabeth L Noey; Yingdong Luo; Liming Zhang; K N Houk
Journal:  J Am Chem Soc       Date:  2011-12-22       Impact factor: 15.419

8.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

9.  Ligand-controlled access to [4 + 2] and [4 + 3] cycloadditions in gold-catalyzed reactions of allene-dienes.

Authors:  Pablo Mauleón; Rachel M Zeldin; Ana Z González; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-05-13       Impact factor: 15.419

10.  Allylic and allenic halide synthesis via NbCl(5)- and NbBr(5)-mediated alkoxide rearrangements.

Authors:  P C Ravikumar; Lihua Yao; Fraser F Fleming
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354
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