TBAF‐Catalyzed Cyclization Reactions of o‐(Alkynyl)phenyl Propargyl Alcohols with Malonate Esters: A Possible Cation–π Interaction as The Activation Approach. Issue 8 (17th February 2020)

• Record Type: Journal Article
• Authors: Zhao, Yulei; Guo, Xuqiang; Wang, Zongkang; Shen, Duyi; Chen, Tingting; Wu, Nan; Yan, Shina; You, Jinmao
• Is Part Of: European journal of organic chemistry. Issue 8(2020)
• Page Start: 978
• Page End: 984
• Publication Date: 2020-02-17
• Subjects: TBAF -- Cation‐π interaction -- Dihydroisobenzofuran -- Malonate ester -- Cyclization reaction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901790
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : 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. Both the basicity of fluoride anion and ammonium cation–π interaction with alkyne unit might play a crucial role in the cyclization reaction.