The Suzuki-Miyaura reaction is by far the most commonly practiced and most powerful of the palladium-catalyzed, cross-coupling reactions. This reaction owes its widespread utility to the vast number of commercially available boronic acids and boronate derivatives as well as the mildness of the reaction conditions and the vast array of ligands that have allowed the coupling of unreactive and challenging substrates. Nevertheless, the molecular details of the critical transmetalation step have remained obscure because of the extreme reactivity of the hypothetical pre-transmetalation intermediate containing the key B–O–Pd linkage. Through<i> </i>the combination of spectroscopic analysis, independent synthesis, and kinetic measurements, we have unambiguously identified and characterized the elusive, pre-transmetalation species that undergo the Suzuki-Miyaura cross-coupling reaction from various boron derivatives. More recently, we have applied the lessons learned from those mechanistic studies to develop an anhydrous, homogeneous cross-coupling process that is both preparatively superior and also mechanistically distinct from the classical reaction.

Mechanistic and preparative aspects of the Suzuki-Miyaura cross-coupling reaction

ACS Spring Meeting 2021

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