Silver-catalyzed direct conversion of epoxides into cyclopropanes using N-triftosylhydrazones

Linxuan Li, Paramasivam Sivaguru, Dandan Wei, Menglin Liu, Qingwen Zhu, Shuai Dong, Emanuele Casali, Nan Li, Giuseppe Zanoni and Xihe Bi ()
Additional contact information
Linxuan Li: Northeast Normal University
Paramasivam Sivaguru: Northeast Normal University
Dandan Wei: Northeast Normal University
Menglin Liu: Northeast Normal University
Qingwen Zhu: Northeast Normal University
Shuai Dong: Northeast Normal University
Emanuele Casali: University of Pavia, Viale Taramelli 12
Nan Li: Northeast Normal University
Giuseppe Zanoni: University of Pavia, Viale Taramelli 12
Xihe Bi: Northeast Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Epoxides, as a prominent small ring O-heterocyclic and the privileged pharmacophores for medicinal chemistry, have recently represented an ideal substrate for the development of single-atom replacements. The previous O-to-C replacement strategy for epoxides to date typically requires high temperatures to achieve low yields and lacks substrate range and functional group tolerance, so achieving this oxygen-carbon exchange remains a formidable challenge. Here, we report a silver-catalyzed direct conversion of epoxides into trifluoromethylcyclopropanes in a single step using trifluoromethyl N-triftosylhydrazones as carbene precursors, thereby achieving oxygen-carbon exchange via a tandem deoxygenation/[2 + 1] cycloaddition. The reaction shows broad tolerance of functional groups, allowing routine cheletropic olefin synthesis in a strategy for the net oxygen-carbon exchange reaction. The utility of this method is further showcased with the late-stage diversification of epoxides derived from bioactive natural products and drugs. Mechanistic experiments and DFT calculations elucidate the reaction mechanism and the origin of the chemo- and stereoselectivity.

Date: 2024
References: View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-024-46188-w Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46188-w

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-024-46188-w

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().