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Base-Assisted Intramolecular C–N Coupling Reaction from NH 2 -Bound Cyclopalladated L -Phenylalanine to Indoline-2-carboxylic Acid

Abstract : 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.
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Submitted on : Friday, August 21, 2020 - 10:56:04 AM
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Aurélien Jacquin-Labarre, Sébastien Coufourier, Rodolphe Tamion, Alexandra Le Foll, Vincent Levacher, et al.. Base-Assisted Intramolecular C–N Coupling Reaction from NH 2 -Bound Cyclopalladated L -Phenylalanine to Indoline-2-carboxylic Acid. Organometallics, American Chemical Society, 2020, 39 (5), pp.767-773. ⟨10.1021/acs.organomet.0c00030⟩. ⟨hal-02493098⟩

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