Intramolecular Arylcyanation of Alkenes Catalyzed by Nickel/AlMe2Cl
- 6 September 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (39), 12874-12875
- https://doi.org/10.1021/ja805088r
Abstract
A catalyst system derived from nickel and cocatalytic AlMe2Cl effects the intramolecular arylcyanation of alkenes. The reaction takes place in an exclusive exo-dig manner to give a wide range of nitriles having a benzylic quaternary carbon in good yields. Detailed investigations are described on the scope and mechanism as well as preliminary results on the asymmetric version of the reaction to provide novel access to chiral quaternary stereocenters.Keywords
This publication has 16 references indexed in Scilit:
- Enantioselective Synthesis of 3,3-Disubstituted Oxindoles through Pd-Catalyzed CyanoamidationOrganic Letters, 2008
- Experimental and Theoretical Examination of C−CN and C−H Bond Activations of Acetonitrile Using Zerovalent NickelJournal of the American Chemical Society, 2007
- Intramolecular cyanoamidation of unsaturated cyanoformamides catalyzed by palladium: an efficient synthesis of multi-functionalized lactamsTetrahedron, 2007
- A Dramatic Effect of Lewis-Acid Catalysts on Nickel-Catalyzed Carbocyanation of AlkynesJournal of the American Chemical Society, 2007
- Cyanoesterification of norbornenes catalyzed by palladium: facile synthetic methodology to introduce cyano and ester functionalities via direct carbon–carbon bond cleavage of cyanoformatesTetrahedron, 2006
- Arylcyanation of alkynes catalyzed by nickelTetrahedron, 2006
- Arylcyanation of Norbornene and Norbornadiene Catalyzed by NickelChemistry Letters, 2006
- Kinetics, Thermodynamics, and Effect of BPh3 on Competitive C−C and C−H Bond Activation Reactions in the Interconversion of Allyl Cyanide by [Ni(dippe)]Journal of the American Chemical Society, 2004
- Catalytic asymmetric synthesis of all-carbon quaternary stereocentersProceedings of the National Academy of Sciences, 2004
- Catalytic hydrocyanation of olefins by nickel(0) phosphite complexes - effects of Lewis acidsOrganometallics, 1984