Journal
ORGANIC LETTERS
Volume 23, Issue 24, Pages 9468-9473Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03650
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Funding
- National University of Kaohsiung
- Ministry of Science and Technology of Taiwan [MOST 110-2628-M-390-001-MY4]
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A carboxylate-assisted palladium-catalyzed Mizoroki-Heck arylation of electron-deficient internal alkenes was developed, utilizing free carboxylic acid as a directing group. The synthetic application demonstrated the potential of this method in decarboxylative aromatization and iodolactonization reactions.
A carboxylate-assisted palladium-catalyzed Mizoroki-Heck arylation of electron-deficient internal alkenes is described herein. This protocol utilized a free carboxylic acid as the directing group for regio- and stereoselective Mizoroki-Heck arylation of beta-cyclohexadienyl acrylates and styrenes with various aryl iodides. The synthetic application has been exhibited by decarboxylative aromatization and iodolactonization/hydrolysis of the resulting polyenes providing trisubstituted alkenes and structurally diverse hydroxyl lactones. Additionally, mechanistic studies have been performed to elucidate the reaction outcome of regio- and stereoselectivity.
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