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Base-Catalyzed Efficient Tandem [3 + 3] and [3 + 2 + 1] Annulation-Aerobic Oxidative Benzannulations

Aboubacar Diallo, Yu-Long Zhao*, He Wang, Sha-Sha Li, Chuan-Qing Ren and Qun Liu*

*Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. China, Email: zhaoyl351nenu.edu.cn, liuqunnenu.edu.cn

A. Diallo, Y.-L. Zhao, H. Wang, S.-S. Li, C.-Q. Ren, Q. Liu, Org. Lett., 2012, 14, 5776-5779.

DOI: 10.1021/ol302829f (free Supporting Information)


Abstract

An efficient base-catalyzed [3 + 3] oxidative aromatization of α,β-unsaturated carbonyl compounds with dimethyl glutaconate under mild, metal-free conditions affords substituted benzenes in high to excellent yields with oxygen as oxidant and water as sole byproduct. In situ generation of the α,β-unsaturated carbonyl compounds from aldehydes and ketones enables a more convenient tandem [3 + 2 + 1] aerobic oxidative aromatization reaction.

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Key Words

arenes, multicomponent reactions, green chemistry, oxygen


ID: J54-Y2012-3690