Nickel Catalyzed syn-Selective Aryl Nickelation and Cyclization of Aldehyde/Enone-Tethered Terminal Alkynes with Arylboronic Acids
A syn-arylative nickelation followed by nucleophilic syn-selective cyclization of o-propargyloxy benzaldehydes is achieved toward the synthesis of chromanol skeletons with alkenyl substitution at C3. The capture of the intermediate vinyl nickel in its cis geometry is done also with a Michael accepto...
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Veröffentlicht in: | Journal of organic chemistry 2018-12, Vol.83 (24), p.15361-15371 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A syn-arylative nickelation followed by nucleophilic syn-selective cyclization of o-propargyloxy benzaldehydes is achieved toward the synthesis of chromanol skeletons with alkenyl substitution at C3. The capture of the intermediate vinyl nickel in its cis geometry is done also with a Michael acceptor to synthesize 4-alkylated derivatives. This protocol is equally applicable to o-propargylamino benzaldehydes to access 3,4-disubstituted tetrahydro-hydroquinolines. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b02618 |