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Synlett 2023; 34(09): 983-989
DOI: 10.1055/s-0041-1738431
DOI: 10.1055/s-0041-1738431
synpacts
Copper(I)-Mediated Decarboxylative N-Arylation of Dioxazolones: Synthesis of N-Aryl Amides
This work was supported by a grant from the National Foundation of Korea (NRF-2021R1F1A1062822) funded by the South Korean government (MSIT). This work was also supported by the Korea Environment Industry and Technology Institute (KEITI) through the Technology Development Program for Safety Management of Household Chemical Products, funded by the Korea Ministry of Environment (MOE)(2022002980)
Abstract
Dioxazolones, which are potent amide precursors, have been widely explored for the formation of C–N bonds with the help of transition-metal catalysts. Here, we highlight our recent studies on the synthesis of N-aryl amides using dioxazolones and boronic acids in the presence of copper(I) chloride under mild conditions. The versatility of the developed reaction is demonstrated by its wide range of functional-group tolerances as well as the release of nontoxic carbon dioxide. Optimization screenings reveal that a fluorine additive improves the desired reactivity toward the intended transformation. The addition of triphenylphosphine results in an N-acyl iminophosphorane, suggesting the involvement of an N-acyl nitrene intermediate in this transformation.
Publication History
Received: 29 November 2022
Accepted after revision: 07 December 2022
Article published online:
03 January 2023
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