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Literature DB >> 29663659

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

Jin Wang¹, Shuyao Zhang¹, Chang Xu², Lukasz Wojtas¹, Novruz G Akhmedov³, Hao Chen², Xiaodong Shi¹.

Abstract

Stereoselective thioallylation of alkynes under possible gold redox catalysis was accomplished with high efficiency (as low as 0.1 % catalyst loading, up to 99 % yield) and broad substrate scope (various alkynes, inter- and intramolecular fashion). The gold(I) catalyst acts as both a π-acid for alkyne activation and a redox catalyst for AuI/III coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for gold redox catalysis without the need for a strong oxidant.

Entities: Chemical

Keywords: alkynes; gold redox catalysis; sulfonium cations; thioallylation; vinyl gold intermediates

Mesh：

Substances：

Year: 2018 PMID： 29663659 PMCID： PMC6121218 DOI： 10.1002/anie.201802540

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

52 in total

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Authors: A Stephen K Hashmi
Journal: Chem Rev Date: 2007-06-20 Impact factor: 60.622

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

Authors: Guozhu Zhang; Yu Peng; Li Cui; Liming Zhang
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3. Mechanistic surprises in the gold(I)-catalyzed intramolecular hydroarylation of allenes.

Authors: Dieter Weber; Michael A Tarselli; Michel R Gagné
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

4. Organogold reactivity with palladium, nickel, and rhodium: transmetalation, cross-coupling, and dual catalysis.

Authors: Joshua J Hirner; Yili Shi; Suzanne A Blum
Journal: Acc Chem Res Date: 2011-06-06 Impact factor: 22.384

5. Combining gold and photoredox catalysis: visible light-mediated oxy- and aminoarylation of alkenes.

Authors: Basudev Sahoo; Matthew N Hopkinson; Frank Glorius
Journal: J Am Chem Soc Date: 2013-04-08 Impact factor: 15.419

6. A Highly Efficient Gold-Catalyzed Photoredox α-C(sp(3))-H Alkynylation of Tertiary Aliphatic Amines with Sunlight.

Authors: Jin Xie; Shuai Shi; Tuo Zhang; Nina Mehrkens; Matthias Rudolph; A Stephen K Hashmi
Journal: Angew Chem Int Ed Engl Date: 2015-03-30 Impact factor: 15.336

7. 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

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. Synthesis and structural characterization of stable organogold(I) compounds. Evidence for the mechanism of gold-catalyzed cyclizations.

Authors: Le-Ping Liu; Bo Xu; Mark S Mashuta; Gerald B Hammond
Journal: J Am Chem Soc Date: 2008-12-31 Impact factor: 15.419

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

1. Gold-catalyzed organic reactions.

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

3. Mechanistic surprises in the gold(I)-catalyzed intramolecular hydroarylation of allenes.

4. Organogold reactivity with palladium, nickel, and rhodium: transmetalation, cross-coupling, and dual catalysis.

5. Combining gold and photoredox catalysis: visible light-mediated oxy- and aminoarylation of alkenes.

6. A Highly Efficient Gold-Catalyzed Photoredox α-C(sp(3))-H Alkynylation of Tertiary Aliphatic Amines with Sunlight.

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

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

9. Synthesis and structural characterization of stable organogold(I) compounds. Evidence for the mechanism of gold-catalyzed cyclizations.

10. Alkyne Difunctionalization by Dual Gold/Photoredox Catalysis.

1. Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.

2. Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant.

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

4. Gold redox catalysis for cyclization/arylation of allylic oximes: synthesis of isoxazoline derivatives.

5. Chiral Hemilabile P,N-Ligand-Assisted Gold Redox Catalysis for Enantioselective Alkene Aminoarylation.

6. Palladium(II)-assisted activation of thioglycosides.