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Synlett 2022; 33(18): 1813-1818
DOI: 10.1055/s-0040-1719866
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Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

Claisen Rearrangement Triggered by Brønsted Acid Catalyzed Alkyne Alkoxylation

Yao-Hong Yan
a   College of Chemistry &Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
,
Long Li∗
a   College of Chemistry &Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
,
Long-Wu Ye∗
b   The Key Laboratory for Chemical Biology of Fujian Province & State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China
c   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› Author AffiliationsWe are grateful for the financial support from the National Natural Science Foundation of China (22125108, 92056104 and 21772161) and from Wenzhou University.
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Abstract

Over the past two decades, catalytic alkyne alkoxylation-initiated Claisen rearrangement has proven to be a practical and powerful strategy for the rapid assembly of a diverse range of structurally complex molecules. The rapid development of Claisen rearrangements triggered by transition-metal-catalyzed alkyne alkoxylation has shown great potential in the formation of carbon–carbon bonds in an atom-economic and mild way. However, metal-free alkyne alkoxylation-triggered Claisen rearrangement has seldom been exploited. Recently, Brønsted acids such as HNTf2 and HOTf have been shown to be powerful activators that promote catalytic alkyne alkoxylation/Claisen rearrangement, leading to the concise and flexible synthesis of valuable compounds with high efficiency and atom economy. Recent advances on the Brønsted acid catalyzed alkyne alkoxylation/Claisen rearrangement are introduced in this Account, in which both intramolecular and intermolecular tandem reactions are discussed.

Keywords

metal-free - Brønsted acid - Claisen rearrangement - alkynes - tandem reaction - alkoxylation


Publication History

Received: 13 November 2021

Accepted after revision: 13 December 2021

Article published online:
13 January 2022

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