Practical Pd(II)-Catalyzed C-H Alkylation with Epoxides: One-Step Syntheses of 3,4-Dihydroisocoumarins.
J Am Chem Soc
; 137(34): 10950-3, 2015 Sep 02.
Article
em En
| MEDLINE
| ID: mdl-26274062
ABSTRACT
Pd(II)-catalyzed ortho-alkylation of benzoic acids with both terminal and internal epoxides affords 3,4-dihydroisocoumarins in one step. The presence of potassium countercations is crucial for this reaction. Monoprotected amino acid ligands significantly promote this reaction, enabling the development of a practical C-H alkylation reaction using 0.5 mol % Pd catalyst. The inversion of stereochemistry in the C-H alkylation step is consistent with a redox-neutral SN2 nucleophilic ring-opening process as opposed to a Pd(II)/Pd(IV) pathway.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article