Cooperative Ni/Vitamin B12-Catalyzed Hydroarylation of Styrene Derivatives with Aryl Iodides

A simple, mild, and scalable methodology enabled by a cooperative nickel/vitamin B12 catalyst was developed for the hydroarylation of styrene derivatives with aryl iodides. Under our optimized conditions, more than 20 substrates bearing different functional groups were tolerated, generating 1,1-diaryl methyl substrates in moderate to excellent yields. The tolerance of our methodology for chloro, bromo, and also B(Pin) functional groups opens the door for further cross-couplings or diverse post-transformations exploiting the wealth of boron chemistry. The scalability of our methodology was demonstrated on a scale of 25 g of the starting material using a 1 L glass double-coated reactor with no notable loss of catalytic activity, without any process development study. Moreover, the synthetic utility of this strategy was illustrated via the synthesis of the racemic mixture of one antiviral agent in one step and with good yield. A couple of mechanistic experiments were also conducted and appear to rule out a radical approach.