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Construction of 3,4-Dihydroisoquinolinones and Indanones via DTBP-Promoted Oxidative Coupling of N-Allylbenzamides with Aromatic Aldehydes

Author:
Xu, Zhong-Qi, Wang, Chao, Li, Lin, Duan, Lili, Li, Yue-Ming
Source:
Journal of organic chemistry 2018 v.83 no.17 pp. 9718-9728
ISSN:
1520-6904
Subject:
aldehydes, chemical bonding, chemical reactions, chemical structure, indans, organic chemistry
Abstract:
A metal-free oxidative tandem coupling of N-allylbenzamide with aryl aldehydes was realized. This method allowed the 1,2-difunctionalization of the C═C double bond in N-allylbenzamides through simultaneous formation of two C(sp²)–C(sp³) bonds. In the presence of DTBP, 4-substituted 3,4-dihydroisoquinolin-1(2H)-ones were obtained in satisfactory isolated yields. 3-Substituted indanones could also be formed by varying the structures of the starting materials.
Agid:
6127033