Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions.

Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions. Research Abstract Details 

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Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions. Abstract Text:

Vasily Kotov,Christopher C Scarborough,Shannon S Stahl,

Palladium-catalyzed methods for the aerobic oxidative coupling of alkenes and oxygen nucleophiles (e.g., water and carboxylic acids) have been known for nearly 50 years. The present account summarizes our development of analogous aerobic oxidative amination reactions, including the first intermolecular aza-Wacker reactions compatible with the use of unactivated alkenes. The reactions are initiated by intra- or intermolecular aminopalladation of the alkene. The resulting alkylpalladium(II) intermediate generally undergoes beta-hydride elimination to produce enamides or allylic amide products, but in certain cases, the Pd-C bond can be trapped to achieve 1,2-difunctionalization of the alkene, including carboamination and aminoacetoxylation. Mechanistic studies have provided a variety of fundamental insights into the reactions, including the effect of ancillary ligands on palladium catalysts, the origin of the Brønsted-base-induced switch in regioselectivity in the oxidative amination of styrene, and evidence that both cis- and trans-aminopalladations of alkenes are possible. Overall, these reactions highlight the potential utility of an "organometallic oxidase" strategy for the selective aerobic oxidation of organic molecules.

Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions. Publishing Authors By Initials

V Kotov,CC Scarborough,SS Stahl,

For similar inorganic chemicals: elements: metals, heavy: palladium research abstracts see: inorganic chemicals: elements: metals, heavy: palladium research

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Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Inorganic chemistry

VOLUME: 46

Page Numbers: 1910-23

Journal Abbreviation:

ISSN: 0020-1669

DAY: 19

MONTH: Mar

YEAR: 2007

Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 366543

Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions. Keywords Mesh Terms:

KEYWORDS: Palladium

MESH TERMS: chemistry

Chemical & Substance for Abstract: Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions. Information

Substance Name: Palladium

Registry Number: 7440-05-3

Grant and Affiliation Information for Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions.

AFFILIATION: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: R01 GM67173

ACRONYM: GM

MEDLINETA: Inorg Chem

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