REDOX REACTIONS INVOLVING N-ALKYL-DIHYDRONICOTINAMIDES

Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl-alkyl Kumada coupling reactions.

Many nickel-based catalysts have been reported for cross-coupling reactions of nonactivated alkyl halides. The mechanistic understanding of these reactions is still primitive. Here we report a mechanistic study of alkyl-alkyl Kumada coupling catalyzed by a preformed nickel(II) pincer complex ([(N2N)Ni-Cl]). The coupling proceeds through a radical process, involving two nickel centers for the ox...

Electrochemical properties of nicotinamide derivatives in aqueous solution - Part IV. Oxidation of N1 -alkyl-1,4-dihydronicotinamides

Nickel-catalyzed cross-coupling reactions involving secondary and tertiary alkyl nucleophiles

Cu-catalyzed oxidative Povarov reactions between N-alkyl N-methylanilines and saturated oxa- and thiacycles.

Cu-catalyzed oxidative Povarov reactions between N,N-dialkylanilines and saturated oxa- or thiacycles with tert-butyl hydroperoxide (TBHP) are described; notably, the reactions use neither [4π] nor [2π]-motifs as the initial reagents. The use of cheap alkane-based substances as building units is of mechanistic and practical interest as two inert sp(3) C-H bonds are activated.

Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds

N-Alkyl-N-chlorosulfonamides add to alkenes under copper(I) catalysis. In reactions of styrene derivatives with terminal double bonds the addition products were obtained in excellent yield and high regioselectivity. Lower yields are obtained in addition reactions to non-aromatic alkenes. The reaction most likely proceeds via a redox catalysis and amidyl radicals, a concerted mechanism has been ...