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Distinct reactivity of Pd(OTs)2: the intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes. 2008

Chris E Houlden, and Chris D Bailey, and J Gair Ford, and Michel R Gagné, and Guy C Lloyd-Jones, and Kevin I Booker-Milburn
School of Chemistry, Cantock's Close, University of Bristol, Bristol, BS8 1TS, UK.

A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl ureas and 1,3-dienes that proceeds under mild conditions in relatively nonacidic media, is presented. The in situ generation, or preformation, of a palladium tosylate emerges as a key parameter in gaining the requisite reactivity for the C-H insertion/carbopalladation/nucleophilic displacement process.

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
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.
D011090 Polyenes Hydrocarbons with more than one double bond. They are a reduced form of POLYYNES. Cumulenes
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
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
D013449 Sulfonamides A group of compounds that contain the structure SO2NH2. Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide
D014050 Toluene A widely used industrial solvent.
D014508 Urea A compound formed in the liver from ammonia produced by the deamination of amino acids. It is the principal end product of protein catabolism and constitutes about one half of the total urinary solids. Basodexan,Carbamide,Carmol

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