5558-87-2Relevant articles and documents
FACILE PALLADIUM CATALYZED DECARBOXYLATIVE ALLYLATION OF ACTIVE METHYLENE COMPOUNDS UNDER NEUTRAL CONDITIONS USING ALLYLIC CARBONATES
Tsuji, Jiro,Shimizu, Isao,Minami, Ichiro,Ohashi, Yukihiro
, p. 4809 - 4812 (1982)
Palladium catalyzed decarboxylative allylation of active methylene compounds proceeded under mild neutral conditions using allylic carbonates, which are much more reactive than allylic acetates or phenoxides used commonly in the reaction.
Efficient and Clean Nickel Catalyzed α-Allylation Reaction of Nitriles
Mouhsine, Bouchaib,Karim, Abdallah,Dumont, Clément,Suisse, Isabelle,Sauthier, Mathieu
supporting information, p. 1457 - 1462 (2021/02/16)
A clean method has been developed for the α-allylation of phenyl and alpha alkyl phenyl acetonitrile with allylic alcohols. The reaction is catalyzed by nickel complexes in situ generated from a combination of Ni(cod)2 and the dppf ligand and performed at 80 °C in methanol as reaction solvent.Accordingly to this simple and base-free protocol that only yields water as a side-product, many allylic nitriles were synthetized with good yields. (Figure presented.).
Surprising and Highly Efficient Use of Methylmagnesium Chloride as a Non-Nucleophilic Base in the Deprotonation and Alkylation of sp3 Centres Adjacent to Nitriles
Gbadebo, Omolola,Smith, Dennis,Harnett, Ger,Donegan, Gregory,O'Leary, Patrick
, p. 7037 - 7045 (2019/01/04)
Methylmagnesium chloride (MeMgCl) is a key reagent in research and industry typically as a nucleophile. In this article we develop the use of MeMgCl as a non-nucleophilic base in conjunction with catalytic amounts of an amine mediator. Specifically, we use the base to deprotonate α to a variety of nitriles in alkylation reactions, applying it to the synthesis of a wide variety of tertiary and quaternary nitriles, including examples where we successively and successfully added three different substituents on the carbon α to the nitrile. This method is generally applicable, high yielding and much greener than existing methods, and it has considerable advantages for industrial application.
Retro-Claisen benzylation: Direct use of benzyl alcohols in Pd-catalyzed couplings with nitriles
Maji, Tapan,Ramakumar, Kinthada,Tunge, Jon A.
supporting information, p. 14045 - 14048 (2015/02/05)
A new strategy has been developed for the benzylation of nitriles directly from benzyl alcohols. In this process benzyl alcohols undergo retro-Claisen activation with cyanoacetic esters to generate an active electrophile and a carbanionic nucleophile. In the presence of Pd(0) these intermediates undergo catalytic coupling to generate a new C - C bond, resulting in the formation of phenyl propionitriles.