Copper(I)-Mediated Decarboxylative N-Arylation of Dioxazolones: Synthesis of N-Aryl Amides

Jinhwan Park; Dongkyu Jang; Jihye An; Yeongmi Park; Hyeonwoong Bae; Minseok Kim; Joohyun Lee; Jongwoo Son

doi:10.1055/s-0041-1738431

Synlett, Table of Contents

Synlett 2023; 34(09): 983-989
DOI: 10.1055/s-0041-1738431

synpacts

Copper(I)-Mediated Decarboxylative N-Arylation of Dioxazolones: Synthesis of N-Aryl Amides

Authors

Jinhwan Park‡

^aDepartment of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
Dongkyu Jang‡

^aDepartment of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
Jihye An

^aDepartment of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
Yeongmi Park

^aDepartment of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea
Hyeonwoong Bae

^bDepartment of Chemistry, Dong-A University, Busan, 49315, South Korea
Minseok Kim

^bDepartment of Chemistry, Dong-A University, Busan, 49315, South Korea
Joohyun Lee

^bDepartment of Chemistry, Dong-A University, Busan, 49315, South Korea
Jongwoo Son∗

^aDepartment of Chemical Engineering (BK21 FOUR Graduate Program), Dong-A University, Busan, 49315, South Korea

^bDepartment of Chemistry, Dong-A University, Busan, 49315, South Korea

Abstract

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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

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References

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