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Literature DB >> 22877083

Regioselectivity switch: gold(I)-catalyzed oxidative rearrangement of propargyl alcohols to 1,3-diketones.

A Stephen K Hashmi¹, Tao Wang, Shuai Shi, Matthias Rudolph.

Abstract

The gold(I)-catalyzed oxidative rearrangement of propargyl alcohols provides an efficient and selective route to 1,3-diketones under mild conditions. Pyridine-N-oxides were used as external oxidants with, different from related substrates, no alkylidenecycloalkanones or oxetan-3-ones formed as side-products.

Entities: Chemical

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Year: 2012 PMID： 22877083 DOI： 10.1021/jo301381z

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

10 in total

1. Enantioselective oxidative gold catalysis enabled by a designed chiral P,N-bidentate ligand.

Authors: Kegong Ji; Zhitong Zheng; Zhixun Wang; Liming Zhang
Journal: Angew Chem Int Ed Engl Date: 2014-11-27 Impact factor: 15.336

2. Gold-Catalyzed Oxidation of Propargylic Ethers with Internal C-C Triple Bonds: Impressive Regioselectivity Enabled by Inductive Effect.

Authors: Kegong Ji; Brendan D'Souza; Jon Nelson; Liming Zhang
Journal: J Organomet Chem Date: 2014-11-01 Impact factor: 2.369

3. Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: efficient oxidative union of allylic sulfides and terminal alkynes via C-C bond formation.

Authors: Jiabin Li; Kegong Ji; Renhua Zheng; Jonathan Nelson; Liming Zhang
Journal: Chem Commun (Camb) Date: 2014-04-21 Impact factor: 6.222

Review 4. Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors: Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal: Chem Rev Date: 2021-02-16 Impact factor: 72.087

5. Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes.

Authors: Kegong Ji; Jonathan Nelson; Liming Zhang
Journal: Beilstein J Org Chem Date: 2013-09-24 Impact factor: 2.883

Regioselectivity switch: gold(I)-catalyzed oxidative rearrangement of propargyl alcohols to 1,3-diketones.

1. Enantioselective oxidative gold catalysis enabled by a designed chiral P,N-bidentate ligand.

2. Gold-Catalyzed Oxidation of Propargylic Ethers with Internal C-C Triple Bonds: Impressive Regioselectivity Enabled by Inductive Effect.

3. Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: efficient oxidative union of allylic sulfides and terminal alkynes via C-C bond formation.

Review 4. Homogeneous Gold-Catalyzed Oxidation Reactions.

5. Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes.

6. Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles.

7. A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes.

8. Selective α-Methylation of Aryl Ketones Using Quaternary Ammonium Salts as Solid Methylating Agents.

9. A non-diazo approach to α-oxo gold carbenes via gold-catalyzed alkyne oxidation.

10. Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes.