Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds.

Advanced Synthesis & Catalysis
Soumitra AgastiDebabrata Maiti

Abstract

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.

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Citations

Mar 3, 2017·The Journal of Organic Chemistry·Mohammad RehanPrasanta Ghorai
Jun 2, 2017·Chemical Communications : Chem Comm·Soumitra AgastiDebabrata Maiti
Dec 8, 2017·Archives of Pharmacal Research·Bing Tian ZhaoMi Hee Woo
Jan 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Michael OschmannOscar Verho
May 21, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lucia ChiummientoPaolo Lupattelli
Mar 22, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·István M MándityFerenc Fülöp
Sep 29, 2020·Chemical Communications : Chem Comm·Geetika RaniKamaldeep Paul
May 25, 2021·Organic & Biomolecular Chemistry·So Won Youn, Cheon-Gyu Cho
Aug 17, 2021·Chemical Communications : Chem Comm·Bhargav DesaiTogati Naveen
Dec 5, 2019·Organic Letters·Liang-Liang ZhaoXiaoyu Yan
Nov 2, 2021·Chemical Communications : Chem Comm·Balaji D BarveWen-Tai Li

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Methods Mentioned

BETA
NMR
column chromatography

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