Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters

Zi-Ying Wang, Shoujun Wang, Nan-Nan Dai, Yao Xiao, Yu Zhou, Wen-Chan Tian, Dongru Sun, Qiang Li, Yong Wang () and Wen-Ting Wei ()
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Zi-Ying Wang: Ningbo University
Shoujun Wang: Ningbo University
Nan-Nan Dai: Ningbo University
Yao Xiao: Ningbo University
Yu Zhou: Ningbo University
Wen-Chan Tian: Ningbo University
Dongru Sun: Ningbo University
Qiang Li: Liaocheng University
Yong Wang: Ningbo University
Wen-Ting Wei: Ningbo University

Nature Communications, 2025, vol. 16, issue 1, 1-8

Abstract: Abstract C–C bond cleavage and recombination provide an efficient strategy for the modification and reconstruction of molecule structures. Herein, we present a method for achieving amidation of aryl C(sp2)–H bond through the cleavage and recombination of C–C triple bond with the involvement of nitrous acid esters. This method marks the instance of precise and controlled stepwise cleavage of C–C triple bond, offering a fresh perspective for the cleavage of such bonds. Nitrous acid ester serves as both a radical source and a hydrogen atom transfer (HAT) reagent to functionalize and utilize the two carbon atoms of the C–C triple bond. The alkoxy radical captures the hydrogen atom from the aryl C(sp2)–H bond or N-hydroxyl to induce the 1,3-oxygen radical migration, which is crucial for the subsequent cleavage of the C–C bond.

Date: 2025
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DOI: 10.1038/s41467-025-56370-3

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