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Triflic Acid‐Catalyzed Enynes Cyclization: A New Strategy beyond Electrophilic π‐Activation
Author(s) -
Yu Zhunzhun,
Liu Lu,
Zhang Junliang
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601599
Subject(s) - triflic acid , electrophile , catalysis , combinatorial chemistry , chemistry , substrate (aquarium) , transition metal , scope (computer science) , organic chemistry , computer science , oceanography , programming language , geology
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.