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Oxidative C–C Bond Functionalization of Methylenecyclopropanes with Aldehydes for the Formation of 2-Acyl-3,4-dihydronaphthalenes

Author:
Liu, Yu, Wang, Qiao-Lin, Zhou, Cong-Shan, Xiong, Bi-Quan, Zhang, Pan-Liang, Yang, Chang-an, Tang, Ke-Wen
Source:
Journal of organic chemistry 2018 v.83 no.8 pp. 4657-4664
ISSN:
1520-6904
Subject:
Lewis acids, aldehydes, carbon, chemical bonding, chemical structure, cyclization reactions, ferrous chloride, organic chemistry
Abstract:
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.
Agid:
6047185