Literature DB >> 20557048

Gold-catalyzed three-component coupling: oxidative oxyarylation of alkenes.

Asa D Melhado1, William E Brenzovich, Aaron D Lackner, F Dean Toste.   

Abstract

The three-component coupling of terminal alkenes with arylboronic acids and oxygen nucleophiles is described. The reaction employs a binuclear gold(I) bromide as a catalyst and Selectfluor reagent as the stoichiometric oxidant. Alcohols, carboxylic acids, and water can be employed as oxygen nucleophiles, thus providing an efficient entry into beta-aryl ethers, esters, and alcohols from alkenes.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20557048      PMCID： PMC2904393          DOI： 10.1021/ja1034123

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


  43 in total

1.  Gold(I)-catalyzed intermolecular addition of phenols and carboxylic acids to olefins.

Authors:  Cai-Guang Yang; Chuan He
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

2.  Gold-catalyzed homogeneous oxidative cross-coupling reactions.

Authors:  Guozhu Zhang; Yu Peng; Li Cui; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Synthesis of aziridines by palladium-catalyzed reactions of allylamines with aryl and alkenyl halides: evidence of a syn-carboamination pathway.

Authors:  Sayuri Hayashi; Hideki Yorimitsu; Koichiro Oshima
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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

Authors:  Alois Fürstner
Journal:  Chem Soc Rev       Date:  2009-07-22       Impact factor: 54.564

5.  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

6.  Alkynes as equivalents of alpha-diazo ketones in generating alpha-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones.

Authors:  Longwu Ye; Li Cui; Guozhu Zhang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

7.  Mechanism of N-fluorobenzenesulfonimide promoted diamination and carboamination reactions: divergent reactivity of a Pd(IV) species.

Authors:  Paul A Sibbald; Carolyn F Rosewall; Rodney D Swartz; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

8.  Gold(I)-catalyzed three-component additions of 2-(arylmethylene)cyclopropylcarbinols, terminal arynes, and alcohols: an efficient access to 3-oxabicyclo[3.1.0]hexanes.

Authors:  Guo-Qiang Tian; Min Shi
Journal:  Org Lett       Date:  2007-10-18       Impact factor: 6.005

9.  A general gold-catalyzed direct oxidative coupling of non-activated arenes.

Authors:  Anirban Kar; Naveenkumar Mangu; Hanns Martin Kaiser; Matthias Beller; Man Kin Tse
Journal:  Chem Commun (Camb)       Date:  2008-01-21       Impact factor: 6.222

10.  A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water.

Authors:  Chunmei Wei; Chao-Jun Li
Journal:  J Am Chem Soc       Date:  2003-08-13       Impact factor: 15.419
View more
  40 in total

1.  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

2.  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

3.  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

4.  Two metals are better than one in the gold catalyzed oxidative heteroarylation of alkenes.

Authors:  Ekaterina Tkatchouk; Neal P Mankad; Diego Benitez; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-08-23       Impact factor: 15.419

Review 5.  Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors:  Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-24       Impact factor: 15.336

6.  Gold-catalyzed allylation of aryl boronic acids: accessing cross-coupling reactivity with gold.

Authors:  Mark D Levin; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-05       Impact factor: 15.336

7.  Pd(0)/Au(I) redox incompatibilities as revealed by Pd-catalyzed homo-coupling of arylgold(I)-complexes.

Authors:  Dieter Weber; Michel R Gagné
Journal:  Chem Commun (Camb)       Date:  2011-03-31       Impact factor: 6.222

8.  Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant.

Authors:  Jin Wang; Shuyao Zhang; Chang Xu; Lukasz Wojtas; Novruz G Akhmedov; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-07       Impact factor: 15.336

9.  Enantioselective synthesis of cyclic carbamimidates via a three-component reaction of imines, terminal alkynes, and p-toluenesulfonylisocyanate using a monophosphine gold(I) catalyst().

Authors:  Matthew J Campbell; F Dean Toste
Journal:  Chem Sci       Date:  2011-05-12       Impact factor: 9.825

10.  Highly selective domino multicyclizations for forming polycyclic fused acridines and azaheterocyclic skeletons.

Authors:  Bo Jiang; Xue Wang; Hai-Wei Xu; Man-Su Tu; Shu-Jiang Tu; Guigen Li
Journal:  Org Lett       Date:  2013-03-18       Impact factor: 6.005
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.