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- Title
Catalytic Behavior of Mono‐N‐Protected Amino‐Acid Ligands in Ligand‐Accelerated C−H Activation by Palladium(II).
- Authors
Salazar, Chase A.; Gair, Joseph J.; Flesch, Kaylin N.; Guzei, Ilia A.; Lewis, Jared C.; Stahl, Shannon S.
- Abstract
Mono‐N‐protected amino acids (MPAAs) are increasingly common ligands in Pd‐catalyzed C−H functionalization reactions. Previous studies have shown how these ligands accelerate catalytic turnover by facilitating the C−H activation step. Here, it is shown that MPAA ligands exhibit a second property commonly associated with ligand‐accelerated catalysis: the ability to support catalytic turnover at substoichiometric ligand‐to‐metal ratios. This catalytic role of the MPAA ligand is characterized in stoichiometric C−H activation and catalytic C−H functionalization reactions. Palladacycle formation with substrates bearing carboxylate and pyridine directing groups exhibit a 50–100‐fold increase in rate when only 0.05 equivalents of MPAA are present relative to PdII. These and other mechanistic data indicate that facile exchange between MPAAs and anionic ligands coordinated to PdII enables a single MPAA to support C−H activation at multiple PdII centers.
- Subjects
LIGANDS (Chemistry); PALLADIUM; CARBON-hydrogen bonds; AMINO acids; HOMOGENEOUS catalysis; HECK reaction; CATALYSIS
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 27, p10965
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202002484