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Synlett 2023; 34(09): 983-989
DOI: 10.1055/s-0041-1738431
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Copper(I)-Mediated Decarboxylative N-Arylation of Dioxazolones: Synthesis of N-Aryl Amides

Jinhwan Park‡
a   Department of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
,
Dongkyu Jang‡
a   Department of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
,
Jihye An
a   Department of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
,
Yeongmi Park
a   Department of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
,
Hyeonwoong Bae
b   Department of Chemistry, Dong-A University, Busan, 49315, South Korea
,
Minseok Kim
b   Department of Chemistry, Dong-A University, Busan, 49315, South Korea
,
Joohyun Lee
b   Department of Chemistry, Dong-A University, Busan, 49315, South Korea
,
Jongwoo Son∗
a   Department of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
b   Department of Chemistry, Dong-A University, Busan, 49315, South Korea
› Author AffiliationsThis 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)
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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.

Key words

copper catalysis - amides - nitrenes - boronic acids - C–N bond formation


Publication History

Received: 29 November 2022

Accepted after revision: 07 December 2022

Article published online:
03 January 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
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