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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| Hauptverfasser: | , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
June 23, 2025
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| In: |
Chemistry - a European journal
Year: 2025, Jahrgang: 31, Heft: 35, Pages: 1-10 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202501015 |
| Online-Zugang: | 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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| Verfasserangaben: | Elmira Jamshidi, Saideh Rajai-Daryasarei, Robert Stranger, Alireza Ariafard, Frank Rominger, and Saeed Balalaie |
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| 245 | 1 | 0 | |a Copper(I)-catalyzed acid-controlled divergent radical cyclization of 1,6-enynes to access 1-indanones and 1H-cyclopropa[b] naphthalene-2,7-diones |c Elmira Jamshidi, Saideh Rajai-Daryasarei, Robert Stranger, Alireza Ariafard, Frank Rominger, and Saeed Balalaie |
| 246 | 3 | 3 | |a Copper(one)-catalyzed acid-controlled divergent radical cyclization of one,six-enynes to access one-indanones and oneH-cyclopropa[b] naphthalene-two,seven-diones |
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| 520 | |a 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. | ||
| 650 | 4 | |a 1-Indanones | |
| 650 | 4 | |a 1,6-Enynes | |
| 650 | 4 | |a 4-Methyl benzoic acid | |
| 650 | 4 | |a Copper(I) Catalysis | |
| 650 | 4 | |a Radical cyclization | |
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| 700 | 1 | |a Stranger, Robert |e VerfasserIn |4 aut | |
| 700 | 1 | |a Ariafard, Alireza |e VerfasserIn |4 aut | |
| 700 | 1 | |a Rominger, Frank |d 1964- |e VerfasserIn |0 (DE-588)1019978228 |0 (DE-627)691067821 |0 (DE-576)359202756 |4 aut | |
| 700 | 1 | |a Balalaie, Saeed |e VerfasserIn |4 aut | |
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