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Electrosynthesis of Highly Functionalized Quinolines through Radical Annulation-Polar Addition Cascade.
- Source :
-
Organic letters [Org Lett] 2024 Sep 06; Vol. 26 (35), pp. 7330-7335. Date of Electronic Publication: 2024 Aug 22. - Publication Year :
- 2024
-
Abstract
- 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.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 26
- Issue :
- 35
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 39172934
- Full Text :
- https://doi.org/10.1021/acs.orglett.4c02470