Elsevier, Tetrahedron, 30-31(64), p. 7437-7443
DOI: 10.1016/j.tet.2008.05.018
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The mechanistic study of the palladium-catalyzed Suzuki–Miyaura cross-coupling between bromophenylpyridine compounds and phenylboronic acid led to the NMR identification of a transient intermediate in the transmetalation step. This species was identified by DFT calculations as a [Pd{Ph-B(OH)3−}{C5H2RN}(PR3)2] complex, containing a boronate ligand coordinated through an oxygen group to the metal center. The fitting of this intermediate within recent mechanistic proposals on the mechanism of transmetalation is discussed.Graphical abstract