Phase-Transfer Catalysts Shift the Pathway to Transmetalation in Biphasic Suzuki–Miyaura Cross-Couplings
Jason Hein and Joshua Derasp report on the use of phase-transfer catalysts in Suzuki–Miyaura cross-couplings.
Since its initial reports in 1979 by Miyaura and Suzuki, the Suzuki–Miyaura coupling (SMC) reaction has become an indispensable tool for carbon-carbon bond formation, earning a share of the 2010 Nobel Prize in Chemistry. Its mild reaction conditions and broad substrate scope have led to widespread applications in pharmaceutical synthesis, medicinal chemistry, natural product synthesis, and polymer synthesis. Despite its broad utility, the dominant mode of transmetalation in SMC reactions remains controversial and highly dependent on the specific reaction conditions employed.
A recent paper published by the group of Professor Jason Hein at the University of British Columbia (Vancouver, Canada) represents a significant advancement in the field of SMC reactions. The study explores the mechanistic intricacies of SMC under biphasic conditions and highlights the pivotal role of phase transfer catalysts (PTCs) in enhancing the reaction rate and shifting the transmetalation pathway and addresses a long-standing controversy in the SMC mechanism, particularly regarding the mode of transmetalation.
Read the full article Phase-Transfer Catalysts Shift the Pathway to Transmetalation in Biphasic Suzuki–Miyaura Cross-Couplings
