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
Hauptverfasser: Liu, Yu, Wang, Qiao-Lin, Zhou, Cong-Shan, Xiong, Bi-Quan, Zhang, Pan-Liang, Yang, Chang-an, Tang, Ke-Wen
Format: Artikel
Sprache:eng
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00427