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Literature DB >> 27754689

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

Jiaming Li¹, Robert H Grubbs¹, Brian M Stoltz¹.

Abstract

A mild aerobic intramolecular aminoacetoxylation method for the synthesis of pyrrolidine and indoline derivatives was achieved using molecular oxygen as the oxidant. A catalytic NOx species acts as an electron transfer mediator to access a high-valent palladium intermediate as the presumed active oxidant.

Entities: Chemical Species

Mesh：

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Year: 2016 PMID： 27754689 PMCID： PMC5512709 DOI： 10.1021/acs.orglett.6b02722

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

39 in total

1. Emergence of palladium(IV) chemistry in synthesis and catalysis.

Authors: Petr Sehnal; Richard J K Taylor; Ian J S Fairlamb
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

2. Palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes with hydrogen peroxide as oxidant.

Authors: Haitao Zhu; Pinhong Chen; Guosheng Liu
Journal: Org Lett Date: 2015-03-05 Impact factor: 6.005

3. The aerobic oxidation of a Pd(II) dimethyl complex leads to selective ethane elimination from a Pd(III) intermediate.

Authors: Julia R Khusnutdinova; Nigam P Rath; Liviu M Mirica
Journal: J Am Chem Soc Date: 2012-01-20 Impact factor: 15.419

4. Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.

Authors: Erik J Alexanian; Chulbom Lee; Erik J Sorensen
Journal: J Am Chem Soc Date: 2005-06-01 Impact factor: 15.419

Review 5. High-valent organometallic copper and palladium in catalysis.

Authors: Amanda J Hickman; Melanie S Sanford
Journal: Nature Date: 2012-04-11 Impact factor: 49.962

6. Catalytic aerobic oxidation of substituted 8-methylquinolines in Pd(II)-2,6-pyridinedicarboxylic acid systems.

Authors: Jing Zhang; Eugene Khaskin; Nicholas P Anderson; Peter Y Zavalij; Andrei N Vedernikov
Journal: Chem Commun (Camb) Date: 2008-06-16 Impact factor: 6.222

7. High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

Authors: Kilian Muñiz
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

8. 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

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

1. Emergence of palladium(IV) chemistry in synthesis and catalysis.

2. Palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes with hydrogen peroxide as oxidant.

3. The aerobic oxidation of a Pd(II) dimethyl complex leads to selective ethane elimination from a Pd(III) intermediate.

4. Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.

Review 5. High-valent organometallic copper and palladium in catalysis.

6. Catalytic aerobic oxidation of substituted 8-methylquinolines in Pd(II)-2,6-pyridinedicarboxylic acid systems.

7. High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

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

9. Enantioselective palladium-catalyzed diamination of alkenes using N-fluorobenzenesulfonimide.

10. Aldehyde-selective Wacker-type oxidation of unbiased alkenes enabled by a nitrite co-catalyst.

1. Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System.

2. Preparation of Key Intermediates for the Syntheses of Coenzyme Q₁₀ and Derivatives by Cross-Metathesis Reactions.