Thianthrenation-Enabled Pyrrolidin-2-yl and Tetrahydrofuran-2-yl Methylation of (Hetero)Arenes

The mild and efficient palladium-catalyzed pyrrolidin-2-yl and tetrahydrofuran-2-yl methylation of (hetero)­arenes has been developed. A wide range of (hetero)­arenes underwent the regioselective thianthrenation to generate the arylthianthrenium triflate, and the developed Pd-catalyzed alkene carboa...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 15; pp. 2606 - 2610
Main Authors Peng, Boyu, Dai, Licheng, Liu, Ruzhang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.04.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CARBOAMINATION REACTIONS
ALKENE
GOLD
CATALYSIS
INSERTION
PHOTOREDOX
SULFONYLATION
CARBOHETEROFUNCTIONALIZATION
OXYARYLATION
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Summary:The mild and efficient palladium-catalyzed pyrrolidin-2-yl and tetrahydrofuran-2-yl methylation of (hetero)­arenes has been developed. A wide range of (hetero)­arenes underwent the regioselective thianthrenation to generate the arylthianthrenium triflate, and the developed Pd-catalyzed alkene carboamination and carboalkoxylation reactions afforded the corresponding biologically important pyrrolidine and tetrahydrofuran derivatives. Mechanistic studies indicated that this reaction proceeds through a syn-heteropalladation mechanistic pathway. The demonstrated late-stage functionalization and enantioselective reaction will help to promote the potential application of the established method in organic synthesis and related fields.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00582