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Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2015 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 357, no 10, 2331-2338 p.Article in journal (Refereed) Published
Abstract [en]

Palladium-catalyzed oxidative annulations between phenols and alkenylcarboxylic acids produced a library of benzofuran compounds. Depending on the nature of the substitution of the phenol precursor, either 2,3-dialkylbenzofurans or 2-alkyl-3-methylene-2,3-dihydrobenzofurans can be synthesized with excellent regioselectivity. Reactions between conjugated 5-phenylpenta-2,4-dienoic acids and phenol gave 3-alkylidenedihydrobenzofuran alkaloid motifs while biologically active 7-arylbenzofuran derivatives were prepared by starting from 2-phenylphenols. More interestingly, selective incorporation of deuterium from D2O has been discovered, which offers an attractive one-step method to access deuterated compounds.

Place, publisher, year, edition, pages
2015. Vol. 357, no 10, 2331-2338 p.
Keyword [en]
benzofurans, C-H activation, deuterium, palladium, synthetic methods
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-119560DOI: 10.1002/adsc.201500308ISI: 000358208000023OAI: oai:DiVA.org:su-119560DiVA: diva2:846794
Funder
Swedish Research Council
Available from: 2015-08-18 Created: 2015-08-17 Last updated: 2017-12-04Bibliographically approved

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