Metal-Free Oxidative C–C Bond Functionalization of Methylenecyclopropanes with Ethers Leading to 2‑Substituted 3,4‑Dihydronaphthalenes

A novel metal-free oxidative ring-opening/cyclization of methylenecyclopropanes with ethers was established for the synthesis of diverse 2-substituted 3,4-dihydronaphthalenes with high selectivity and efficiency. This oxidative cyclization is achieved by C­(sp3)-H functionalization, ring-opening, an...

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Veröffentlicht in:Journal of organic chemistry 2017-07, Vol.82 (14), p.7394-7401
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 novel metal-free oxidative ring-opening/cyclization of methylenecyclopropanes with ethers was established for the synthesis of diverse 2-substituted 3,4-dihydronaphthalenes with high selectivity and efficiency. This oxidative cyclization is achieved by C­(sp3)-H functionalization, ring-opening, and cyclization, and this method represents a new example of methylenecyclopropane oxidative cyclization with an aromatic carbon and a C­(sp3)-H bond by simultaneously forming two new carbon–carbon bonds.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00970