PdI2‑Catalyzed Regioselective Cyclocarbonylation of 2‑Allyl Phenols to Dihydrocoumarins

PdI2‑Catalyzed Regioselective Cyclocarbonylation of 2‑Allyl Phenols to Dihydrocoumarins

A simple, efficient, and regioselective synthesis of 3-methyl-3,4-dihydro­coumarins is reported. The reaction of 2-allyl phenols with synthesis gas was catalyzed by PdI2, and 1,3,5,7-tetra­methyl-6-phenyl-2,4,8-trioxa-6-phos­pha­adaman­tane (L1) and 1,3,5,7-tetra­methyl-6-tetra­decyl-2,4,8-trioxa-6-...

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Veröffentlicht in:Organic letters 2014-11, Vol.16 (22), p.5827-5829
Hauptverfasser: Amézquita-Valencia, Manuel, Alper, Howard
Format: Artikel
Sprache:eng
Schlagworte:
Adamantane - analogs & derivatives
Adamantane - chemistry
Catalysis
Coumarins - chemical synthesis
Coumarins - chemistry
Cyclization
Ligands
Molecular Structure
Palladium - chemistry
Phenols - chemistry
Stereoisomerism
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Zusammenfassung:A simple, efficient, and regioselective synthesis of 3-methyl-3,4-dihydro­coumarins is reported. The reaction of 2-allyl phenols with synthesis gas was catalyzed by PdI2, and 1,3,5,7-tetra­methyl-6-phenyl-2,4,8-trioxa-6-phos­pha­adaman­tane (L1) and 1,3,5,7-tetra­methyl-6-tetra­decyl-2,4,8-trioxa-6-phospha­adaman­tane (L2) were effective as ligands, affording good product selectivity in all cases.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5029157