Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 34, Pages 10950-10953Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b07507
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Funding
- Scripps Research Institute
- NSF under CCI Center [CHE-1205646]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1205646] Funding Source: National Science Foundation
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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 S(N)2 nucleophilic ring-opening process as opposed to a Pd(II)/Pd(IV) pathway.
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