Journal
ORGANIC LETTERS
Volume 13, Issue 1, Pages 146-149Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1027283
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- EPSRC
- Royal Society
- Leverhulme Trust
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Abnormal reactivity has been observed in Negishi, Suzuki Miyaura, and Kumada Tamao Corriu cross-couplings in which PEPPSI-IPr (where PEPPSI stands for pyridine enhanced precatalyst preparation, stabilization, and initiation and IPr refers to the NHC ligand) is employed, implicating the presence of two distinct Pd-0 species in the catalytic cycle. Polybrominated arenes and organometallic reagents react selectively to give the product of exhaustive polysubstitution regardless of the initial reaction stoichiometry. Competition experiments suggest that, after an initial activation controlled oxidative addition, reductive elimination produces an ultrareactive Pd-0 species which consumes all remaining C-Br bonds in the molecule under diffusion control.
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