Literature DB >> 20050647

Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes.

Guozhu Zhang1, Li Cui, Yanzhao Wang, Liming Zhang.   

Abstract

Homogeneous carboamination, carboalkoxylation and carbolactonization of terminal alkenes are realized via oxidative gold catalysis, providing expedient access to various substituted N- or O-heterocycles. Deuterium-labeling studies established the anti nature of the alkene functionalization and the indispensible role of Au(I)/Au(III) catalysis. This study constitutes the first example of catalytically converting C(sp(3))-Au bonds into C(sp(3))--C(sp(2)) bonds in a cross-coupling manner and opens new opportunities to study gold alkene catalysis where alkylgold intermediates can be readily functionalized intermolecularly.

Entities:  

Year:  2010        PMID: 20050647     DOI: 10.1021/ja909555d

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


  56 in total

1.  Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions.

Authors:  Brandon R Rosen; Joshua E Ney; John P Wolfe
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

2.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

3.  C-C coupling reactivity of an alkylgold(III) fluoride complex with arylboronic acids.

Authors:  Neal P Mankad; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

4.  Highly diastereoselective Pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans.

Authors:  Amanda F Ward; John P Wolfe
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

5.  Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.

Authors:  Lei Miao; Imranul Haque; Maria R Manzoni; Weng Siong Tham; Sherry R Chemler
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

6.  Application of fundamental organometallic chemistry to the development of a gold-catalyzed synthesis of sulfinate derivatives.

Authors:  Miles W Johnson; Scott W Bagley; Neal P Mankad; Robert G Bergman; Vincent Mascitti; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-20       Impact factor: 15.336

7.  Alkylgold complexes by the intramolecular aminoauration of unactivated alkenes.

Authors:  Rebecca L Lalonde; William E Brenzovich; Diego Benitez; Ekaterina Tkatchouk; Kotaro Kelley; William A Goddard; F Dean Toste
Journal:  Chem Sci       Date:  2010-08-01       Impact factor: 9.825

8.  Synthesis of saturated 1,4-benzodiazepines via Pd-catalyzed carboamination reactions.

Authors:  Joshua D Neukom; Alvin S Aquino; John P Wolfe
Journal:  Org Lett       Date:  2011-03-29       Impact factor: 6.005

9.  Recent Developments in Pd-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles.

Authors:  Danielle M Schultz; John P Wolfe
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

10.  Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines.

Authors:  Joshua J Hirner; Katrina E Roth; Yili Shi; Suzanne A Blum
Journal:  Organometallics       Date:  2012-10-08       Impact factor: 3.876

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