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TBAF‐Catalyzed Cyclization Reactions of o ‐(Alkynyl)phenyl Propargyl Alcohols with Malonate Esters: A Possible Cation–π Interaction as The Activation Approach
Author(s) -
Zhao Yulei,
Guo Xuqiang,
Wang Zongkang,
Shen Duyi,
Chen Tingting,
Wu Nan,
Yan Shina,
You Jinmao
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901790
Subject(s) - chemistry , malonate , propargyl , alkyne , nucleophile , catalysis , nucleophilic addition , medicinal chemistry , diethyl malonate , combinatorial chemistry , conjugate , organic chemistry , mathematical analysis , mathematics
An efficient method has been devised for the synthesis of dihydroisobenzofuran derivatives through the reaction of in situ generated ynones with potentially C‐nucleophilic malonate esters. All the products are capable to be prepared by applying the tandem strategy at room temperature. The reaction was realized through a combination of the pivotal TBAF‐catalyzed conjugate addition and selective O ‐nucleophilic cyclization. As revealed by the control experiments, both the basicity of fluoride anion and ammonium cation–π interaction with alkyne unit might play crucial roles in the cyclization reaction.