BIOMAT Database Logo BIOMAT Database Logo

Aerobic oxidative amination of unactivated alkenes catalyzed by palladium. 2005

Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.

The first examples of palladium-catalyzed oxidative amination of unactivated alkyl olefins have been identified. To be successful, these reactions must be conducted under cocatalyst-free conditions that involve direct dioxygen-coupled turnover of the palladium catalyst. The oxidative amination products of norbornene and other cyclic alkenes implicate a cis-aminopalladation mechanism.

UI MeSH Term Description Entries
D007097 Imines Organic compounds containing a carbon-nitrogen double bond where a NITROGEN atom can be attached to HYDROGEN or an alkyl or aryl group. Imine
D009636 Norbornanes Compounds that include or are derivatives of norbornane(bicyclo[2.2.1]heptane). Norbornane Derivatives,Norbornene Derivatives,Norbornenes,Norcamphanes,Derivatives, Norbornane,Derivatives, Norbornene
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D010165 Palladium A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D000332 Aerobiosis Life or metabolic reactions occurring in an environment containing oxygen. Aerobioses
D000475 Alkenes Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408) Alkene,Olefin,Olefins,Pentene,Pentenes
D000586 Amination The creation of an amine. It can be produced by the addition of an amino group to an organic compound or reduction of a nitro group. Aminations
D000588 Amines A group of compounds derived from ammonia by substituting organic radicals for the hydrogens. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amine

Related Publications

Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Aerobic intramolecular oxidative amination of alkenes catalyzed by NHC-coordinated palladium complexes.
May 2006, Organic letters,
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Copper-Catalyzed Intramolecular Oxidative Amination of Unactivated Internal Alkenes.
March 2016, Chemistry (Weinheim an der Bergstrasse, Germany),
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Regioselective palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes.
October 2013, Chemical communications (Cambridge, England),
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Palladium-catalyzed intermolecular aerobic oxidative amination of terminal alkenes: efficient synthesis of linear allylamine derivatives.
January 2008, Angewandte Chemie (International ed. in English),
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions.
March 2007, Inorganic chemistry,
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Palladium-Catalyzed Oxidative Amination of Unactivated Olefins with Primary Aliphatic Amines.
May 2023, Journal of the American Chemical Society,
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Enantioselective palladium-catalyzed diarylation of unactivated alkenes.
November 2019, Chemical communications (Cambridge, England),
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Asymmetric Palladium-Catalyzed Aminochlorination of Unactivated Alkenes.
April 2023, Organic letters,
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
Palladium-catalyzed intramolecular aminofluorination of unactivated alkenes.
November 2009, Journal of the American Chemical Society,
Jodie L Brice, and Jenna E Harang, and Vitaliy I Timokhin, and Natia R Anastasi, and Shannon S Stahl
An intermolecular palladium-catalyzed diamination of unactivated alkenes.
October 2010, Angewandte Chemie (International ed. in English),
Copied contents to your clipboard!