Ru‐Catalyzed Deoxygenative Functionalization of Phenols via π‐Coordination Activation: Mechanochemical Access to N‐Aryl Amides and α‐Aryl Carbonyls

Given the vast occurrence and availability of both primary amides and phenols, the synthesis of N-aryl amides via direct coupling between these starting materials would be much attractive. Herein, we report an efficient method for the mechanochemical synthesis of N-aryl amides via ruthenium-catalyzed direct amidation of unprotected phenols with primary amides with water as the sole byproduct. Unexpectedly, replacing amides with methyl carboxylic acids, esters, or ketones, the same reaction led to the formation of α-aryl carbonyl derivatives instead of the anticipated aryl carboxylates. The synthetic strategy accepts a wide scope of primary amides, alkyl carbonyls, and phenolic substrates to deliver 28 expected N-aryl amides and 14 unexpected α-aryl carbonyl derivatives with good to excellent yields. The developed synthetic approach would serve as the better alternative to the classical cross-coupling reactions in context to the PASE (pot, atom, and step economy) synthesis and late-stage modification of structurally complex molecules, including natural products and pharmaceuticals.

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Journal
Chemistry - A European Journal
Published
2025-05-07
DOI
https://doi.org/10.1002/chem.202500862
Primary Topic
Chemical Synthesis and Analysis
Type
article
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0.00

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article

Ru‐Catalyzed Deoxygenative Functionalization of Phenols via π‐Coordination Activation: Mechanochemical Access to N‐Aryl Amides and α‐Aryl Carbonyls

Vitaliy Yepishev, Ronak V. Prajapati, Viktor O. Iaroshenko, Yevhen Karpun et al.
1 links
Chemistry - A European Journal
Chemical Synthesis and Analysis
article

Ru‐Catalyzed Deoxygenative Functionalization of Phenols via π‐Coordination Activation: Mechanochemical Access to N‐Aryl Amides and α‐Aryl Carbonyls

Vitaliy Yepishev, Ronak V. Prajapati, Viktor O. Iaroshenko, Yevhen Karpun, Oleksandr Shalimov, Vaibhav D. Prajapati, Satenik Mkrtchyan, Gabriela Addová, Juraj Filo, Vishal B. Purohit
article en

Abstract

Given the vast occurrence and availability of both primary amides and phenols, the synthesis of N-aryl amides via direct coupling between these starting materials would be much attractive. Herein, we report an efficient method for the mechanochemical synthesis of N-aryl amides via ruthenium-catalyzed direct amidation of unprotected phenols with primary amides with water as the sole byproduct. Unexpectedly, replacing amides with methyl carboxylic acids, esters, or ketones, the same reaction led to the formation of α-aryl carbonyl derivatives instead of the anticipated aryl carboxylates. The synthetic strategy accepts a wide scope of primary amides, alkyl carbonyls, and phenolic substrates to deliver 28 expected N-aryl amides and 14 unexpected α-aryl carbonyl derivatives with good to excellent yields. The developed synthetic approach would serve as the better alternative to the classical cross-coupling reactions in context to the PASE (pot, atom, and step economy) synthesis and late-stage modification of structurally complex molecules, including natural products and pharmaceuticals.

Chemistry - A European JournalVol. 31(34)
National Academy of Sciences of Ukraine (UA), Gulf University for Science & Technology (KW), National University of Life and Environmental Sciences of Ukraine (UA), Charotar University of Science and Technology (IN), Interregional Academy of Personnel Management (UA), Institute of Organic Chemistry (UA), Sardar Patel Renewable Energy Research Institute (IN), Georgian American University (GE), Sardar Patel University (IN), Matej Bel University (SK), Chitkara University (IN), Comenius University Bratislava (SK)
Agentúra na Podporu Výskumu a Vývoja
Openalex Percentile: Top 91%
Chemical Synthesis and Analysis
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