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1 article(s) from Lee, Seungmin

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

Seungmin Lee,
Minsuk Kim,
Hyewon Han and
Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

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Graphical Abstract

Scheme 1: Formation of isocyanates and amidated arenes from dioxazolones.

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Scheme 2: Copper-catalyzed synthesis of δ-lactams via open-shell copper nitrenoid transfer. ^aCuBr (10 mol %) ...

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Figure 1: Proposed reaction pathway for the copper-catalyzed synthesis of δ-lactams from dioxazolones.

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Scheme 3: Copper(II)-catalyzed synthesis of 1,2,4-triazole derivatives.

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Figure 2: Proposed reaction mechanism for the copper-catalyzed synthesis of 1,2,4-triazole analogues from dio...

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Scheme 4: Copper(I)-catalyzed synthesis of N-acyl amidines from dioxazolones, acetylenes, and amines. ^aPerfor...

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Figure 3: Proposed reaction mechanism for the copper(I)-catalyzed synthesis of N-acyl amidines.

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Scheme 5: Preparation of N-arylamides from dioxazolones and boronic acids using a copper salt.

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Figure 4: Proposed reaction pathway for the copper-mediated synthesis of N-arylamides from dioxazolones.

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Scheme 6: Copper-catalyzed preparation of N-acyl iminophosphoranes from dioxazolones.

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Figure 5: Proposed reaction pathway for the copper-catalyzed synthesis of N-acyl iminophosphoranes from dioxa...

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Scheme 7: Copper-catalyzed synthesis of N-acyl sulfenamides. ^a1.0 equiv of 18 and 2.0 equiv of 19 were used. ^b...

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Figure 6: Proposed reaction mechanism for the copper-catalyzed S-amidation of thiols.

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Scheme 8: Copper-catalyzed asymmetric hydroamidation of vinylarenes. ^a4 mol % + 2 mol % catalyst was used. ^b4...

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Figure 7: Proposed reaction mechanism for the copper-catalyzed hydroamidation of vinylarenes.

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Scheme 9: Copper-catalyzed anti-Markovnikov hydroamidation of alkynes.

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Figure 8: Proposed reaction mechanism for the copper-catalyzed amidation of alkynes.

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Scheme 10: Copper-catalyzed preparation of primary amides through N–O bond reduction using reducing agent.

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Figure 9: Proposed catalytic cycle for the copper-catalyzed reduction of dioxazolones.

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Review

Published 22 Jan 2025

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