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Regioselective Synthesis of 4,5‐Dihydro‐6 H ‐oxepino[3,2‐ c ]chromene‐2,6(3 H )‐diones through Palladium‐Catalyzed Intramolecular Alkoxycarbonylation of 3‐Allyl‐4‐hydroxycoumarins
Author(s) -
Sosa D. Oliver,
Almaraz Karla,
AmézquitaValencia Manuel
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900649
Subject(s) - regioselectivity , chemistry , palladium , intramolecular force , catalysis , carbonylation , ring (chemistry) , medicinal chemistry , substrate (aquarium) , organic chemistry , carbon monoxide , oceanography , geology
Seven‐membered ring lactones fused to coumarin scaffolds were obtained via a palladium‐catalyzed regioselective intramolecular alkoxycarbonylation under a CO atmosphere. Cyclocarbonylation of 3‐allyl‐4‐hydroxycoumarin derivatives was accessed in the absence of hydrogen gas, acidic conditions, or any other additives. The results of the control experiments revealed the importance of pKa of the substrate for initiating the reaction.