Tosylhydrazide-induced 1,6-enyne radical cyclization under copper catalysis: access to 3,4-dihydronaphthalen-1(2H)-one derivatives
We describe an approach to access 4-aroyl-3-aryl-3,4-dihydronaphthalen-1(2H)-one derivatives in 41-79% yields through the Cu-catalyzed radical cyclization/desulfonylation of 1,6-enynes with tosylhydrazide under air conditions. This alternative desulfonylation strategy combines mild conditions, exter...
Gespeichert in:
| Hauptverfasser: | , , , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
20 September 2024
|
| In: |
The journal of organic chemistry
Year: 2024, Jahrgang: 89, Heft: 18, Pages: 13575-13584 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.4c01746 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.4c01746
|
| Verfasserangaben: | Yeganeh Sadat Hosseini Nasab, Saideh Rajai-Daryasarei, Frank Rominger, Saeed Balalaie |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1903050979 | ||
| 003 | DE-627 | ||
| 005 | 20241205173402.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240920s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.joc.4c01746 |2 doi | |
| 035 | |a (DE-627)1903050979 | ||
| 035 | |a (DE-599)KXP1903050979 | ||
| 035 | |a (OCoLC)1475312734 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Hosseini Nasab, Yeganeh Sadat |e VerfasserIn |0 (DE-588)1342550099 |0 (DE-627)1903051711 |4 aut | |
| 245 | 1 | 0 | |a Tosylhydrazide-induced 1,6-enyne radical cyclization under copper catalysis |b access to 3,4-dihydronaphthalen-1(2H)-one derivatives |c Yeganeh Sadat Hosseini Nasab, Saideh Rajai-Daryasarei, Frank Rominger, Saeed Balalaie |
| 246 | 3 | 3 | |a Tosylhydrazide-induced one,six-enyne radical cyclization under copper catalysis |
| 264 | 1 | |c 20 September 2024 | |
| 300 | |b Illustrationen | ||
| 300 | |a 10 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Online veröffentlicht: 30. August 2024 | ||
| 500 | |a Gesehen am 20.09.2024 | ||
| 520 | |a We describe an approach to access 4-aroyl-3-aryl-3,4-dihydronaphthalen-1(2H)-one derivatives in 41-79% yields through the Cu-catalyzed radical cyclization/desulfonylation of 1,6-enynes with tosylhydrazide under air conditions. This alternative desulfonylation strategy combines mild conditions, external oxidant-free processes, and sustainability, contributing to more environmentally friendly organic synthesis. The mechanistic studies showed that the CuCl/O2 combination serves as the source of the oxygen atom needed to form the C═O bond. The existence of tosylhydrazide is crucial for this conversion. | ||
| 700 | 1 | |a Rajai-Daryasarei, Saideh |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 | |
| 773 | 0 | 8 | |i Enthalten in |t The journal of organic chemistry |d [Erscheinungsort nicht ermittelbar] : American Chemical Society, 1936 |g 89(2024), 18 vom: Sept., Seite 13575-13584 |h Online-Ressource |w (DE-627)268133387 |w (DE-600)1472273-2 |w (DE-576)090854292 |x 1520-6904 |7 nnas |a Tosylhydrazide-induced 1,6-enyne radical cyclization under copper catalysis access to 3,4-dihydronaphthalen-1(2H)-one derivatives |
| 773 | 1 | 8 | |g volume:89 |g year:2024 |g number:18 |g month:09 |g pages:13575-13584 |g extent:10 |a Tosylhydrazide-induced 1,6-enyne radical cyclization under copper catalysis access to 3,4-dihydronaphthalen-1(2H)-one derivatives |
| 856 | 4 | 0 | |u https://doi.org/10.1021/acs.joc.4c01746 |x Verlag |x Resolving-System |z lizenzpflichtig |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20240920 | ||
| 993 | |a Article | ||
| 994 | |a 2024 | ||
| 998 | |g 1019978228 |a Rominger, Frank |m 1019978228:Rominger, Frank |d 120000 |d 120100 |e 120000PR1019978228 |e 120100PR1019978228 |k 0/120000/ |k 1/120000/120100/ |p 3 | ||
| 999 | |a KXP-PPN1903050979 |e 4581908876 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"recId":"1903050979","physDesc":[{"extent":"10 S.","noteIll":"Illustrationen"}],"name":{"displayForm":["Yeganeh Sadat Hosseini Nasab, Saideh Rajai-Daryasarei, Frank Rominger, Saeed Balalaie"]},"id":{"doi":["10.1021/acs.joc.4c01746"],"eki":["1903050979"]},"relHost":[{"language":["eng"],"note":["Gesehen am 25.08.2020"],"type":{"media":"Online-Ressource","bibl":"periodical"},"origin":[{"publisherPlace":"[Erscheinungsort nicht ermittelbar]","dateIssuedDisp":"1936-","publisher":"American Chemical Society","dateIssuedKey":"1936"}],"title":[{"title":"The journal of organic chemistry","title_sort":"journal of organic chemistry","subtitle":"web edition"}],"part":{"extent":"10","volume":"89","year":"2024","text":"89(2024), 18 vom: Sept., Seite 13575-13584","pages":"13575-13584","issue":"18"},"corporate":[{"role":"isb","display":"American Chemical Society"}],"disp":"Tosylhydrazide-induced 1,6-enyne radical cyclization under copper catalysis access to 3,4-dihydronaphthalen-1(2H)-one derivativesThe journal of organic chemistry","id":{"issn":["1520-6904"],"eki":["268133387"],"zdb":["1472273-2"]},"pubHistory":["1.1936/37 -"],"recId":"268133387","physDesc":[{"extent":"Online-Ressource"}]}],"person":[{"given":"Yeganeh Sadat","role":"aut","family":"Hosseini Nasab","display":"Hosseini Nasab, Yeganeh Sadat"},{"role":"aut","given":"Saideh","display":"Rajai-Daryasarei, Saideh","family":"Rajai-Daryasarei"},{"role":"aut","given":"Frank","family":"Rominger","display":"Rominger, Frank"},{"role":"aut","given":"Saeed","display":"Balalaie, Saeed","family":"Balalaie"}],"language":["eng"],"origin":[{"dateIssuedKey":"2024","dateIssuedDisp":"20 September 2024"}],"note":["Online veröffentlicht: 30. August 2024","Gesehen am 20.09.2024"],"titleAlt":[{"title":"Tosylhydrazide-induced one,six-enyne radical cyclization under copper catalysis"}],"title":[{"subtitle":"access to 3,4-dihydronaphthalen-1(2H)-one derivatives","title_sort":"Tosylhydrazide-induced 1,6-enyne radical cyclization under copper catalysis","title":"Tosylhydrazide-induced 1,6-enyne radical cyclization under copper catalysis"}],"type":{"bibl":"article-journal","media":"Online-Ressource"}} | ||
| SRT | |a HOSSEININATOSYLHYDRA2020 | ||