Electrosynthesis of Highly Functionalized Quinolines through Radical Annulation–Polar Addition Cascade

Synthesis of diversely functionalized quinoline-2-carboxylates is illustrated through electrochemical cross-dehydrogenative coupling between N-aryl glycinates and methylenecyclopropanes. An extensive range of distinct functionalities is well-compatible under these transition-metal- and oxidant-free...

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Bibliographic Details
Published in:Organic letters 2024-09, Vol.26 (35), p.7330-7335
Main Authors: Saha, Suman Kumar, Mallick, Samrat, Nath, Aritra, De Sarkar, Suman
Format: Article
Language:English
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Summary:Synthesis of diversely functionalized quinoline-2-carboxylates is illustrated through electrochemical cross-dehydrogenative coupling between N-aryl glycinates and methylenecyclopropanes. An extensive range of distinct functionalities is well-compatible under these transition-metal- and oxidant-free mild electrochemical conditions, contributing to a broad substrate scope and practical applicability. Cyclic voltammetric measurements and control experiments suggested a formal [4 + 2] cycloaddition involving radical intermediates, followed by a cyclopropyl ring opening through nucleophilic polar addition, consecutively fabricating C–C and C–N bonds.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02470