Dual role of nitroarenes as electrophiles and arylamine surrogates in Buchwald–Hartwig-type coupling for C–N bond construction

Lei, Zhiguo; Yao, Jiaxin; Xiao, Yuxuan; Liu, Wenbo H.; Yu, Lin; Duan, Wengui; Li, Chao-Jun

doi:10.1039/d3sc06618e

Chem. Sci.

2024

DOI: 10.1039/d3sc06618e

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Dual role of nitroarenes as electrophiles and arylamine surrogates in Buchwald–Hartwig-type coupling for C–N bond construction

Zhiguo Lei,

Jiaxin Yao,

Yuxuan Xiao

et al.

Abstract: One of the most widely utilized methods for the construction of C(sp2)–N bonds is the transition-metal-catalyzed cross-coupling of aryl halides/boronic acids with amines, known as Ullmann condensation, Buchwald-Hartwig amination, and...

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Cited by 9 publications

References 75 publications

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Denitrative Functionalization of Nitroarenes: Recent Progress and Future Perspectives

Li,

Lei,

Yang

et al. 2024

Eur J Org Chem

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Nitroarenes are fundamental feedstocks in the chemical industry. Their relatively inert C−NO2 bond allows for late‐stage modifications of molecules and exhibits complete orthogonality to the reactivity of C−halogen bond in cross‐coupling reactions. The denitrative functionalization of nitroarenes holds significant appeal due to it avoids the use of aryl halides, thereby simplifying reaction steps and improving atom and step economy. Recent progress in direct denitrative functionalization of nitroarenes includes palladium‐catalyzed denitrative coupling, copper‐catalyzed denitrative coupling, as well as metal‐free one‐pot C−NO2 functionalization. In this review, we provide a concise overview of these advancements, detailing the reaction features and mechanisms. This summary aims to highlight the versatility and efficiency of denitrative functionalization methodologies, offering insights into their potential applications and inspiring further research in this promising area of organic synthesis.

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Denitrative Functionalization of Nitroarenes: Recent Progress and Future Perspectives

Li,

Lei,

Yang

et al. 2024

Eur J Org Chem

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Hydroxylamine‐O‐Sulfonic Acid (HOSA): A Recent Synthetic Overview

Kumar,

Divedi,

Chandra

et al. 2024

ChemistrySelect

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Hydroxylamine‐O‐sulfonic acid has been used as a versatile nitrogen source in synthetic organic chemistry. It has dual function and utilized both as a nucleophile and an electrophile during different synthetic transformations. This reagent is stable and easy to handle in both aqueous and organic solvents. It can be used with different functional groups under mild reaction conditions, making its widely applicable for constructing complex molecules. It has been utilized for various applications such as agrochemicals, pharmaceuticals, and polymer industries in the formation of S−N, C−N, O−N, and N−N bonds, as well as for efficient cyclization reactions under metal‐free conditions with excellent stereo– and regioselectivity. The present review provides a brief overview of all the advancements made in the past two decades using hydroxylamine‐O‐sulfonic acid as a nitrogen source.

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Direct Synthesis of α-Ketoamides via Copper-Catalyzed Reductive Amidation of Nitroarenes with α-Oxocarboxylic Acids

Liu,

Yao,

et al. 2024

J. Org. Chem.

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Nitroarenes are known for their stability, low toxicity, easy availability, and cost-effectiveness, making them one of the most fundamental chemical feedstocks. The direct utilization of nitroarenes as nitrogen sources in amidation reactions offers significant advantages over using arylamines. Herein, we disclose a streamlined method for constructing α-ketoamides through the direct coupling of nitroarenes with α-oxocarboxylic acids. This transformation obviates the need for preparing, isolating, and purifying arylamines, leading to improved efficiency, costeffectiveness, and time savings.

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Dual role of nitroarenes as electrophiles and arylamine surrogates in Buchwald–Hartwig-type coupling for C–N bond construction

Abstract: One of the most widely utilized methods for the construction of C(sp2)–N bonds is the transition-metal-catalyzed cross-coupling of aryl halides/boronic acids with amines, known as Ullmann condensation, Buchwald-Hartwig amination, and...

Cited by 9 publications

References 75 publications

Denitrative Functionalization of Nitroarenes: Recent Progress and Future Perspectives

Denitrative Functionalization of Nitroarenes: Recent Progress and Future Perspectives

Hydroxylamine‐O‐Sulfonic Acid (HOSA): A Recent Synthetic Overview

Direct Synthesis of α-Ketoamides via Copper-Catalyzed Reductive Amidation of Nitroarenes with α-Oxocarboxylic Acids

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