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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...

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Bibliographic Details
Main Authors: Hosseini Nasab, Yeganeh Sadat (Author) , Rajai-Daryasarei, Saideh (Author) , Rominger, Frank (Author) , Balalaie, Saeed (Author)
Format: Article (Journal)
Language:English
Published: 20 September 2024
In: The journal of organic chemistry
Year: 2024, Volume: 89, Issue: 18, Pages: 13575-13584
ISSN:1520-6904
DOI:10.1021/acs.joc.4c01746
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.4c01746
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Author Notes:Yeganeh Sadat Hosseini Nasab, Saideh Rajai-Daryasarei, Frank Rominger, Saeed Balalaie
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Summary: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.
Item Description:Online veröffentlicht: 30. August 2024
Gesehen am 20.09.2024
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/acs.joc.4c01746

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