In(III)/PhCO₂H Binary Acid Catalyzed Tandem [2 + 2] Cycloaddition and Nazarov Reaction between Alkynes and Acetals

Lihui Zhu, Zhi-Guo Xi, Jian Lv and Sanzhong Luo*

*CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China, Email: luosziccas.ac.cn

L. Zhu, Z.-G. Xi, J. Lv, S. Luo, Org. Lett., 2013, 15, 4496-4499.

DOI: 10.1021/ol4020464

Abstract

The combination of In(OTf)₃ and benzoic acid synergistically promotes the coupling of alkynes and acetals to form 2,3-disubstituted indanones in excellent yield and diastereoselectivity via a tandem [2 + 2] cycloaddition and Nazarov reaction.

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proposed mechanism

Key Words

Nazarov Reaction, Indanones

ID: J54-Y2013

In(III)/PhCO2H Binary Acid Catalyzed Tandem [2 + 2] Cycloaddition and Nazarov Reaction between Alkynes and Acetals

Lihui Zhu, Zhi-Guo Xi, Jian Lv and Sanzhong Luo*

In(III)/PhCO₂H Binary Acid Catalyzed Tandem [2 + 2] Cycloaddition and Nazarov Reaction between Alkynes and Acetals