C(sp)-heteroatom bond formation by iron-catalyzed soft couplings.

Carbon-heteroatom bonds are of great importance due to their prevalence in pharmaceuticals, agrochemicals, materials, and natural products. Despite the effective use of metal-catalyzed cross-coupling reactions between sp-hybridized organohalides and soft heteroatomic nucleophiles for carbon-heteroatom bond formation, the use of sp-hybridized organohalides remain limited and the coupling with thiols remains elusive. Here, we report the coupling of sp-hybridized benzyl or tertiary halides with soft thiol nucleophiles catalyzed by iron and extend the utility to alcohol and amine nucleophiles.