Synthetic methods: The Ni-catalyzed alkylation of 2-(methylthio)benzothiazoles through CS bond cleavage is reported. Reactions with various secondary alkyl nucleophiles proceeded efficiently in the presence of 1,3-butadiene as an additive. This reaction was proposed to proceed by σ-bond metathesis between the thioether and a bis(π-allyl)nickel complex or by an addition/elimination mechanism involving the CN double bond of the benzothiazoles (see scheme).
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