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通过碳-氮键裂解，由叔胺和羧酸光氧化还原驱动合成酰胺。

Photoredox Driven Amide Synthesis from Tertiary Amines and Carboxylic Acids via C-N Bond Cleavage.

作者信息

Dogan Merve, Akgul Irem, Emmert Marion H, Yilmaz Ozgur

机构信息

Department of Chemistry, Faculty of Sciences, Mersin University, Mersin 33343, Turkey.

Discovery Chemistry, MRL, Merck & Co. Inc., 770 Sumneytown Pike, West Point, Pennsylvania 19486, United States.

出版信息

ACS Omega. 2025 Jul 23;10(30):33755-33766. doi: 10.1021/acsomega.5c04718. eCollection 2025 Aug 5.

DOI:10.1021/acsomega.5c04718
PMID:40787389
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12332612/
Abstract

This manuscript describes a visible-light-promoted, Ir-catalyzed, aerobic protocol for amide synthesis from tertiary amines and carboxylic acids. The reaction likely proceeds through α-C-H oxidation of the tertiary amine, followed by C-N bond cleavage via hydrolysis to the secondary amine intermediate. Concurrently, the additive CFSONa reacts to activate the carboxylic acid via an acyl fluoride intermediate, which in turn reacts with the secondary amine to yield the product amides. The established conditions tolerate a wide variety of carboxylic acid substrates, including complex carboxylic acids. Furthermore, previously unreactive amine substrates such as -methyl morpholine and tri--butyl amine are shown to react readily.

摘要

本手稿描述了一种可见光促进、铱催化的由叔胺和羧酸合成酰胺的需氧方法。该反应可能通过叔胺的α-C-H氧化进行，随后通过水解使C-N键断裂生成仲胺中间体。同时，添加剂CFSONa通过酰氟中间体反应活化羧酸，该中间体进而与仲胺反应生成产物酰胺。所建立的条件能耐受多种羧酸底物，包括复杂的羧酸。此外，以前不反应的胺底物如N-甲基吗啉和三正丁胺也能很容易地发生反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/5f593515e99c/ao5c04718_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/259552fe17b4/ao5c04718_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/21cc8fb4a4af/ao5c04718_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/46969172d490/ao5c04718_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/ccfe4a4d319e/ao5c04718_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/48e370b25b6b/ao5c04718_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/8e72bca91886/ao5c04718_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/1165fc0c4029/ao5c04718_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/1fe49c2c2507/ao5c04718_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/aaece8c3f991/ao5c04718_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/5f593515e99c/ao5c04718_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/259552fe17b4/ao5c04718_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/21cc8fb4a4af/ao5c04718_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/46969172d490/ao5c04718_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/ccfe4a4d319e/ao5c04718_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/48e370b25b6b/ao5c04718_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/8e72bca91886/ao5c04718_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/1165fc0c4029/ao5c04718_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/1fe49c2c2507/ao5c04718_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/aaece8c3f991/ao5c04718_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70c8/12332612/5f593515e99c/ao5c04718_0002.jpg

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本文引用的文献

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Mild and Functional Group-Tolerant Aerobic -Dealkylation of Tertiary Amines Promoted by Photoredox Catalysis.光氧化还原催化促进的温和且官能团容忍的有氧叔胺脱烷基化反应。
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