Ligand-Accelerated ortho-C–H Alkylation of Arylcarboxylic Acids using Alkyl Boron Reagents

Ligand-Accelerated ortho-C–H Alkylation of Arylcarboxylic Acids using Alkyl Boron Reagents

A protocol for the Pd(II)-catalyzed ortho-C–H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupl...

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Veröffentlicht in:Journal of the American Chemical Society 2013-11, Vol.135 (46), p.17508-17513
Hauptverfasser: Thuy-Boun, Peter S, Villa, Giorgio, Dang, Devin, Richardson, Paul, Su, Shun, Yu, Jin-Quan
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
amino acids
Benzoates - chemistry
benzoic acids
boron
Boron Compounds - chemistry
Catalysis
Ligands
Molecular Structure
Palladium - chemistry
Phenylacetates - chemistry
potassium
standard operating procedures
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Zusammenfassung:A protocol for the Pd(II)-catalyzed ortho-C–H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja409014v