The first general method for the reductive dimerization of alkyl halides, alkyl mesylates, alkyl trifluoroacetates, and allylic acetates is reported which proceeds with low catalyst loading (0.5 to 5 mol%), generally high yields (80% ave yield), and good functional-group tolerance.

A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

Alkylated terpyridine ligands are an increasingly important component of catalysis and dyes but are costly because their synthesis is challenging and often low-yielding. We report an improved method for the Pd/C-catalyzed dehydrogenative coupling of 4-picoline to form the bi- and terpyridine. The addition of MnO2 improves the yield of the reaction, making the reaction useful on a large scale (up to 200 mmol). The use of Pd(OAc)2 or Pd/C/pivalic acid leads to the selective formation of bipyridine.

Nickel-Catalyzed, Sodium Iodide-Promoted Reductive Dimerization of AlkylHalides, Alkyl Pseudohalides, and Allylic Acetates. -The unprecedented title reaction proceeds with low catalyst loading (0.5 to 5 mol%), generally high yields (in average 80%) and good functional group tolerance. -(PRINSELL, M. R.; EVERSON, D. A.; WEIX*, D.

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