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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Electrosynthesis of Highly Functionalized Quinolines through Radical Annulation-Polar Addition Cascade
Suman Kumar Saha1, Samrat Mallick1, Aritra Nath1
1Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur-741246, West Bengal, India.
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.
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