Catalytic carbon-carbon bond formation based on cross-coupling reactions (CCRs) plays a central role in the production of natural products, pharmaceuticals, agrochemicals, and organic materials. Coupling reactions with organometallic reagents and organic halides facilitate a plethora of bond-forming reactions in modern synthetic chemistry.
The problem, however, with all current cross-coupling reactions is that they lead to the formation of the stoichiometric production of waste products, such as in:
- the Suzuki CCR boronic acid;
- the Negishi CCR organozinc waste;
- the Stille CCR organotin waste; and
- Kumada organomagnesium.
The Smith Lab has developed silicon-based transfer agents for palladium-mediated cross-coupling processes to yield aryl-aryl, alkenyl-aryl, and alkenyl-alkenyl coupled products. This reaction can occur in one pot with high yield and purity of the product, while eliminating the problems of lithium-halogen exchange, homocoupling from other palladium-mediated methods, including the Suzuki organoboron, Negishi organozinc, Stille organotin, and Kumada organomagnesium, and the stoichiometric production of waste products.
Synthetic overview of silicon-based cross-coupling reaction. From Smith et al, 2012.