Nickel-Catalyzed Coupling of Thiomethyl-Substituted 1,3-Benzothiazoles with Secondary Alkyl Grignard Reagents.

Synthetic methods: The Ni‐catalyzed alkylation of 2‐(methylthio)benzothiazoles through CS 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 CN double bond of the benzothiazoles (see scheme). [ABSTRACT FROM AUTHOR]