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Literature DB >> 24410719

Catalyst-controlled Wacker-type oxidation: facile access to functionalized aldehydes.

Zachary K Wickens¹, Kacper Skakuj, Bill Morandi, Robert H Grubbs.

Abstract

The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceutical agent, atomoxetine. Finally, the influence of proximal functional groups on this anti-Markovnikov reaction was explored, providing important preliminary mechanistic insight.

Entities: Chemical

Year: 2014 PMID： 24410719 DOI： 10.1021/ja411749k

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

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Cited

10 in total

1. Aerobic palladium-catalyzed dioxygenation of alkenes enabled by catalytic nitrite.

Authors: Zachary K Wickens; Pablo E Guzmán; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2014-11-06 Impact factor: 15.336

2. Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate.

Authors: Jiaming Li; Robert H Grubbs; Brian M Stoltz
Journal: Org Lett Date: 2016-10-18 Impact factor: 6.005

3. Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation.

Authors: Crystal K Chu; Daniel T Ziegler; Brian Carr; Zachary K Wickens; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2016-05-25 Impact factor: 15.336

4. The formyloxyl radical: electrophilicity, C-H bond activation and anti-Markovnikov selectivity in the oxidation of aliphatic alkenes.

Authors: Miriam Somekh; Mark A Iron; Alexander M Khenkin; Ronny Neumann
Journal: Chem Sci Date: 2020-10-02 Impact factor: 9.825

5. The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16'-epi-Leucophyllidine.

Authors: Christopher E Reimann; Aurapat Ngamnithiporn; Kohei Hayashida; Daisuke Saito; Katerina M Korch; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2021-07-06 Impact factor: 16.823

6. Total Synthesis of Leiodermatolide A via Transfer Hydrogenative Allylation, Crotylation, and Propargylation: Polyketide Construction beyond Discrete Allyl- or Allenylmetal Reagents.

Authors: Yuk-Ming Siu; James Roane; Michael J Krische
Journal: J Am Chem Soc Date: 2021-07-08 Impact factor: 16.383

Catalyst-controlled Wacker-type oxidation: facile access to functionalized aldehydes.

1. Aerobic palladium-catalyzed dioxygenation of alkenes enabled by catalytic nitrite.

2. Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate.

3. Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation.

4. The formyloxyl radical: electrophilicity, C-H bond activation and anti-Markovnikov selectivity in the oxidation of aliphatic alkenes.

5. The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16'-epi-Leucophyllidine.

6. Total Synthesis of Leiodermatolide A via Transfer Hydrogenative Allylation, Crotylation, and Propargylation: Polyketide Construction beyond Discrete Allyl- or Allenylmetal Reagents.

7. Synthesis of the C(1)-C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C-C Bond Formation.

Review 8. Application of Coordination Compounds with Transition Metal Ions in the Chemical Industry-A Review.

9. Catalytic Isohypsic-Redox Sequences for the Rapid Generation of C_sp3 -Containing Heterocycles.

Review 10. Efficient Aerobic Oxidation of Organic Molecules by Multistep Electron Transfer.