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Chemistry. 2016 Jun 13;22(25):8488-92. doi: 10.1002/chem.201601599. Epub 2016 May 3.

Triflic Acid-Catalyzed Enynes Cyclization: A New Strategy beyond Electrophilic π-Activation.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. China.
2
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. China. lliu@chem.ecnu.edu.cn.
3
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. China. jlzhang@chem.ecnu.edu.cn.
4
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, P. R. China. jlzhang@chem.ecnu.edu.cn.

Abstract

The cyclization of enynes, catalyzed by a transition metal, represents a powerful tool to construct an array of cyclic compounds through electrophilic π-activation. In this paper, we disclose a new and efficient strategy for enynes cyclization catalyzed by triflic acid. The salient features of this transformation includes a broad substrate scope, metal free synthesis, open flask and mild conditions, good yields, ease of operation, low catalyst loading, and easy scale-up to gram scale. A preliminary mechanism study demonstrated that the activation model of the reaction was σ-activation, which is different from the transition-metal-catalyzed enynes cyclization. Our strategy affords a complementary method to the traditional strategies, which use transition-metal catalysts.

KEYWORDS:

enynes; organic chemistry; synthetic methods; triflic acid; σ-activation

PMID:
27124814
DOI:
10.1002/chem.201601599

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