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Literature DB >> 21028911

Gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes.

William E Brenzovich¹, Jean-François Brazeau, F Dean Toste.

Abstract

During continuing studies with a novel oxidative gold oxyarylation reaction, arylsilanes were found to be competent coupling partners, providing further evidence for an intramolecular electrophilic aromatic substitution mechanism. While providing yields complementary to those of the previously described boronic acid methods, the use of trimethylsilanes reduces the observation of homocoupling byproducts and allows for facile intramolecular coupling reactions.

Entities: CellLine Chemical Disease Gene

Mesh：

Substances：
Silanes
Gold

Year: 2010 PMID： 21028911 PMCID： PMC2967413 DOI： 10.1021/ol102194c

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

30 in total

1. Improvements in cross coupling reactions of hypervalent siloxane derivatives.

Authors: M E Mowery; P DeShong
Journal: Org Lett Date: 1999-12-30 Impact factor: 6.005

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. Relativistic functional groups: aryl carbon-gold bond formation by selective transmetalation of boronic acids.

Authors: David V Partyka; Matthias Zeller; Allen D Hunter; Thomas G Gray
Journal: Angew Chem Int Ed Engl Date: 2006-12-11 Impact factor: 15.336

4. Palladium-mediated fluorination of arylboronic acids.

Authors: Takeru Furuya; Hanns Martin Kaiser; Tobias Ritter
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

5. 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

6. Oxidative interception of the hydroamination pathway: a gold-catalyzed diamination of alkenes.

Authors: Alvaro Iglesias; Kilian Muñiz
Journal: Chemistry Date: 2009-10-12 Impact factor: 5.236

7. Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide

Authors:
Journal: J Org Chem Date: 2000-08-25 Impact factor: 4.354

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

Authors: Asa D Melhado; William E Brenzovich; Aaron D Lackner; F Dean Toste
Journal: J Am Chem Soc Date: 2010-07-07 Impact factor: 15.419

9. 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

10. 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

24 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

10. Pinene-derived iminodiacetic acid (PIDA): a powerful ligand for stereoselective synthesis and iterative cross-coupling of C(sp3) boronate building blocks.

Authors: Junqi Li; Martin D Burke
Journal: J Am Chem Soc Date: 2011-08-10 Impact factor: 15.419

Gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes.

1. Improvements in cross coupling reactions of hypervalent siloxane derivatives.

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

3. Relativistic functional groups: aryl carbon-gold bond formation by selective transmetalation of boronic acids.

4. Palladium-mediated fluorination of arylboronic acids.

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

6. Oxidative interception of the hydroamination pathway: a gold-catalyzed diamination of alkenes.

7. Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide

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

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

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

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

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

3. Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach.

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

5. Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents.

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

7. Stable Au(I) catalysts for oxidant-free C-H Functionalization with Iodoarenes.

8. Silicon Incorporated Morpholine Antifungals: Design, Synthesis, and Biological Evaluation.

9. C(sp(3))-F reductive elimination from alkylgold(iii) fluoride complexes.

10. Pinene-derived iminodiacetic acid (PIDA): a powerful ligand for stereoselective synthesis and iterative cross-coupling of C(sp3) boronate building blocks.