From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

Wang, Dong‐Yu; Yang, Zekun; Wang, Chao; Zhang, Ao; Uchiyama, Masanobu

doi:10.1002/ange.201712618

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Angewandte Chemie

2018

DOI: 10.1002/ange.201712618

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From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

Dong‐Yu Wang

Zekun Yang

Chao Wang

et al.

Abstract: We have developed a simple and direct method for the synthesis of aryl ethers by reacting alcohols/phenols (ROH) with aryl ammonium salts (ArNMe3+), which are readily prepared from anilines (ArNR′2, R′=H or Me). This reaction proceeds smoothly and rapidly (within a few hours) at room temperature in the presence of a commercially available base, such as KOtBu or KHMDS, and has a broad substrate scope with respect to both ROH and ArNR′2. It is scalable and compatible with a wide range of functional groups.

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Cited by 14 publications

References 49 publications

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Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

et al. 2020

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A transition‐metal‐free approach to benzyl sulfones by using sodium sulfinates and benzyl ammonium salts is described. The protocol provides a simple and direct method to realize the C−N bond cleavage in the presence of readily available Cs2CO3. During the reaction process, a range of functional groups with respect to both sodium sulfinates and benzylic ammonium salts were well compatible, leading to various benzyl sulfones in moderate to good yields.

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Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

et al. 2020

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Selective Functionalization of Aminoheterocycles by a Pyrylium Salt

et al. 2018

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The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry‐BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C−N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C−O, C−N, C−S, or C−SO2R bonds are disclosed herein. In contrast to C−N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional‐group tolerance. In addition to small‐molecule derivatization, Pyry‐BF4 allows the introduction of functional groups in a late‐stage fashion to furnish highly functionalized structures.

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para‐Selective C−H Borylation of Aromatic Quaternary Ammonium and Phosphonium Salts

Zheng

et al. 2022

Angewandte Chemie

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Aromatic ammonium and phosphonium salts are important synthetic intermediates and multifunctional materials, but para-selective functionalization of the aromatic salts remains a challenge. Here we develop an ionic ligand based on our newly designed "biphenylphenanthroline" skeleton and realize the Ir-catalyzed para-selective CÀ H borylation of seven types of aromatic quaternary ammonium and phosphonium salts. Gram-scale transformation, late-stage elaboration for drug molecule, and diversification of borylated products demonstrate the potential utility of this reaction. The mechanistic studies and computational analysis elucidate the origin of para-selectivity.

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From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

Cited by 14 publications

References 49 publications

Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

Selective Functionalization of Aminoheterocycles by a Pyrylium Salt

para‐Selective C−H Borylation of Aromatic Quaternary Ammonium and Phosphonium Salts

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