Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 51, Pages 17851-17856Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b10680
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Funding
- Spanish MINECO (SGPI) [CTQ2016-80913-P, BES-2014-067770]
- Junta de Castilla y Leon [VA062G18, VAOS1P17]
- UVa
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The ligand [2,2'-bipyridin]-6(1H)-one (bipy-6-OH) has a strong accelerating effect on the Pd-catalyzed direct arylation of pyridine or arenes. The isolation of relevant intermediates and the study of their decomposition unequivocally show that the deprotonated coordinated ligand acts as a base and assists the cleavage of the C-H bond. Mechanistic work indicates that the direct arylation of pyridine with this ligand occurs through a Pd(0)/Pd(II) cycle. Because of this dual ligand-intramolecular base role, there is no need for an available coordination site on the metal for an external base, a difficulty encountered when chelating ligands are used in coupling reactions that involve a C-H cleavage step.
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