Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 37, Pages 14728-14735Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b06643
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Funding
- Welch Foundation [E-0044]
- NIGMS [R01GM077635]
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1-Aminopyridinium ylides are efficient directing groups for palladium-catalyzed beta-arylation and alkylation of sp(3) C-H bonds in carboxylic acid derivatives. The efficiency of these directing groups depends on the substitution at the pyridine moiety. The unsubstituted pyridine-derived ylides allow functionalization of primary C-H bonds, while methylene groups are unreactive in the absence of external ligands. 4-Pyrrolidinopyridine-containing ylides are capable of C-H functionalization in acyclic methylene groups in the absence of external ligands, thus rivaling the efficiency of the aminoquinoline directing group. Preliminary mechanistic studies have been performed. A cyclopalladated intermediate has been isolated and characterized by X-ray crystallography, and its reactivity was studied.
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