Organocatalytic diboration involving "reductive addition" of a boron-boron σ-bond to 4,4'-bipyridine.

J Am Chem Soc

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

Published: March 2015

A 4,4'-bipyridine-based catalyst system for diboration of pyrazine derivatives was established. The catalyst cycle consists of the following two steps: (1) reductive addition of the boron-boron bond of bis(pinacolato)diboron to 4,4'-bipyridine to form N,N'-diboryl-4,4'-bipyridinylidene and (2) oxidative boryl transfer from the intermediate to pyrazine to give N,N'-diboryl-1,4-dihydropyrazine with regeneration of 4,4'-bipyridine.

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http://dx.doi.org/10.1021/jacs.5b00546DOI Listing

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