Chemo-controlled cross-coupling of Di(hetero)aryl disulfides with grignard reagents: C-C vs. C-S bond formation

Abstract

A general protocol for the chemoselectivity-controlled C-C and C-S coupling reactions of di(hetero)aryl disulfides with Grignard reagents catalyzed by ferrocene and palladium acetate has been developed. Ferrocene favored the formation of C-S coupled products at low temperature, whereas C-C bond couplings were favored when palladium acetate was used. All the reactions proceeded with excellent chemoselectivity and in good yields under mild conditions, and a library of molecules with pyridine and pyrimidine scaffolds was produced.