Base-Assisted Intramolecular C–N Coupling Reaction from NH2‑Bound Cyclopalladated l‑Phenylalanine to Indoline-2-carboxylic Acid

The deprotonative intramolecular-amination reaction of phenylalanine-derived palladacycles has been investigated to highlight a facile carbonate-assisted N–H activation before the C–N bond formation. A major counterion effect led to divergent pathways whereby the SPhos-Pd complexes with iodine, trif...

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Bibliographic Details
Published in:Organometallics 2020-03, Vol.39 (5), p.767-773
Main Authors: Jacquin-Labarre, Aurélien, Coufourier, Sébastien, Tamion, Rodolphe, Le Foll, Alexandra, Levacher, Vincent, Afonso, Carlos, Gandon, Vincent, Journot, Guillaume, Brière, Jean-François, Hoarau, Christophe
Format: Article
Language:English
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Summary:The deprotonative intramolecular-amination reaction of phenylalanine-derived palladacycles has been investigated to highlight a facile carbonate-assisted N–H activation before the C–N bond formation. A major counterion effect led to divergent pathways whereby the SPhos-Pd complexes with iodine, triflate, or trifluoroacetate anions were key intermediates to afford access to (S)-2-indolinecarboxylic acid derivatives.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.0c00030