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Gold-catalyzed regio- and stereoselective α-acyloxy-β-alkynylation of ynol ethers

Enol esters and conjugated enynes are valuable structural motifs for synthetic chemistry and material sciences. Herein, the synthesis of tetra-substituted enol ester 2-iodobenzoate derivatives was achieved in good yields at room temperature through a gold-catalyzed acyloxyalkynylation of sensitive y...

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Main Authors: Liu, Yaowen (Author) , Han, Chunyu (Author) , Shi, Hongwei (Author) , Mackenroth, Alexandra (Author) , Zhang, Linghua (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 17 February 2023
In: The journal of organic chemistry
Year: 2023, Volume: 88, Issue: 5, Pages: 2908-2920
ISSN:1520-6904
DOI:10.1021/acs.joc.2c02597
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.2c02597
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Author Notes:Yaowen Liu, Chunyu Han, Hongwei Shi, Alexandra V. Mackenroth, Linghua Zhang, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary:Enol esters and conjugated enynes are valuable structural motifs for synthetic chemistry and material sciences. Herein, the synthesis of tetra-substituted enol ester 2-iodobenzoate derivatives was achieved in good yields at room temperature through a gold-catalyzed acyloxyalkynylation of sensitive ynol ethers with ethynylbenziodoxolones (EBXs), the latter acting as bifunctional reactants. The conversion is highly regioselective with a broad substrate scope. Mechanistically, an Au(III) species is the key intermediate of an Au(I)/Au(III) redox cycle. The reaction is synthetically useful and can easily be scaled up to gram scale.
Item Description:Gesehen am 27.03.2023
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/acs.joc.2c02597

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