Silver-catalyzed site-selective C(sp3)−H benzylation of ethers with N-triftosylhydrazones

Zhaohong Liu, Hongwei Wang, Paramasivam Sivaguru, Steven P. Nolan, Qingmin Song, Weijie Yu, Xinyu Jiang, Edward A. Anderson and Xihe Bi ()
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Zhaohong Liu: Northeast Normal University
Hongwei Wang: Northeast Normal University
Paramasivam Sivaguru: Northeast Normal University
Steven P. Nolan: Ghent University
Qingmin Song: Northeast Normal University
Weijie Yu: Northeast Normal University
Xinyu Jiang: Northeast Normal University
Edward A. Anderson: University of Oxford
Xihe Bi: Northeast Normal University

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract The insertion of carbenes into the α-C–H bonds of ethers represents one of the most powerful approaches to access polysubstituted α-branched ethers. However, intermolecular carbene insertions remain challenging, since current approaches are generally limited to the use of toxic and potentially explosive α-diazocarbonyl compounds. We now report a silver-catalyzed α-C–H benzylation of ethers using bench-stable N-triftosylhydrazones as safe and convenient carbene precursors. This approach is well suited for both inter- and intramolecular insertions to deliver medicinally relevant homobenzylic ethers and 5–8-membered oxacycles in good yields. The synthetic utility of this strategy is demonstrated by its easy scalability, broad scope with valuable functional groups, high regioselectivity, and late-stage functionalization of complex oxygen-containing molecules. The relative reactivities of different types of silver carbenes and C−H bonds were also investigated by experments and DFT calculations.

Date: 2022
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DOI: 10.1038/s41467-022-29323-3

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