Gold-Catalyzed C(sp 3 )-C(sp 2 ) Suzuki-Miyaura Coupling Reaction.

A gold-catalyzed C(sp 3 )-C(sp 2 ) Suzuki-Miyaura coupling reaction facilitated by ligand-enabled Au(I)/Au(III) redox catalysis was developed. The cross-coupling of alkyl organometallics was first realized in the redox catalytic cycle in gold chemistry, without the use of external oxidants. This gold-catalyzed C(sp 3 )-C(sp 2 ) coupling reaction allows a variety of alkyl chain and useful methyl trifluoroborates to react with aryl and vinyl iodides under very mild conditions, which provides a new reactivity pattern for challenging couplings with alkyl organometallics.