Oxidative C–C Bond Functionalization of Methylenecyclopropanes with Aldehydes for the Formation of 2‑Acyl-3,4-dihydronaphthalenes
A new FeCl2- and DTBP (di-tert-butyl peroxide)-promoted oxidative ring-opening and cyclization of methylenecyclopropanes with aldehydes for the synthesis of 2-acyl-3,4-dihydronaphthalenes is presented. This oxidative cyclization reaction proceeds via a radical addition, ring-opening, and cyclization...
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Veröffentlicht in: | Journal of organic chemistry 2018-04, Vol.83 (8), p.4657-4664 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A new FeCl2- and DTBP (di-tert-butyl peroxide)-promoted oxidative ring-opening and cyclization of methylenecyclopropanes with aldehydes for the synthesis of 2-acyl-3,4-dihydronaphthalenes is presented. This oxidative cyclization reaction proceeds via a radical addition, ring-opening, and cyclization sequence facilitated by a Lewis acid, and it offers a practical and straightforward route for the oxidative cyclization of methylenecyclopropanes with an aromatic carbon and a C(sp2)–H bond by simultaneously forming two new carbon–carbon bonds. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b00427 |