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Copper(I)-catalyzed acid-controlled divergent radical cyclization of 1,6-enynes to access 1-indanones and 1H-cyclopropa[b] naphthalene-2,7-diones

Abstract 1-Indanone derivatives are efficiently synthesized via a radical cyclization reaction of 1,6-enynes, using TBHP as both oxidant and reactant, in the presence of Cu(I) as the catalyst and 4-methyl benzoic acid as the cocatalyst. Notably, in the absence of 4-methyl benzoic acid, the reaction...

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Main Authors: Jamshidi, Elmira (Author) , Rajai-Daryasarei, Saideh (Author) , Stranger, Robert (Author) , Ariafard, Alireza (Author) , Rominger, Frank (Author) , Balalaie, Saeed (Author)
Format: Article (Journal)
Language:English
Published: June 23, 2025
In: Chemistry - a European journal
Year: 2025, Volume: 31, Issue: 35, Pages: 1-10
ISSN:1521-3765
DOI:10.1002/chem.202501015
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.202501015
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202501015
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Author Notes:Elmira Jamshidi, Saideh Rajai-Daryasarei, Robert Stranger, Alireza Ariafard, Frank Rominger, and Saeed Balalaie
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Summary:Abstract 1-Indanone derivatives are efficiently synthesized via a radical cyclization reaction of 1,6-enynes, using TBHP as both oxidant and reactant, in the presence of Cu(I) as the catalyst and 4-methyl benzoic acid as the cocatalyst. Notably, in the absence of 4-methyl benzoic acid, the reaction undergoes a dramatic shift in product selectivity, yielding 1H?cyclopropa[b]naphthalene-2,7-diones exclusively under the same conditions, with Cu(I) acting as the sole catalyst. This transformation offers key advantages, including operational simplicity, cost-effective and readily available materials, scalability to gram quantities, and compatibility with a wide range of functional groups. Mechanistic studies and DFT calculations confirmed that the reaction proceeds through a radical pathway, highlighting the pivotal role of 4-methylbenzoic acid as the cocatalyst in altering product selectivity.
Item Description:Zuerst veröffentlicht: 07. April 2025
Gesehen am 15.09.2025
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202501015

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