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Dr. Arash Ghaderi, Dr. Takanori Iwasaki, Asuka Fukuoka, Prof. Dr. Jun Terao and Prof. Dr. Nobuaki Kambe Nickel-Catalyzed Coupling of Thiomethyl-Substituted 1,3-Benzothiazoles with Secondary Alkyl Grignard Reagents Chemistry - A European Journal 19

Version of Record online: 25 JAN 2013 | DOI: 10.1002/chem.201203413

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Synthetic methods: The Ni-catalyzed alkylation of 2-(methylthio)benzothiazoles through C[BOND]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[DOUBLE BOND]N double bond of the benzothiazoles (see scheme).

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