Literature DB >> 29431295

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

Dong-Yu Wang1,2, Ze-Kun Yang3,4, Chao Wang3,4, Ao Zhang1,2,5, Masanobu Uchiyama3,4.   

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 KOt Bu 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.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−N cleavage; C−O formation; amines; ethers; late-stage functionalization

Year:  2018        PMID: 29431295     DOI: 10.1002/anie.201712618

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  3 in total

1.  Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.

Authors:  Mixiang Tian; Lidong Shao; Xiaosan Su; Xuhong Zhou; Honglei Zhang; Kun Wei; Ruifen Sun; Junliang Wang
Journal:  RSC Adv       Date:  2022-06-27       Impact factor: 4.036

2.  Selective single C-F bond arylation of trifluoromethylalkene derivatives.

Authors:  Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

3.  From aniline to phenol: carbon-nitrogen bond activation via uranyl photoredox catalysis.

Authors:  Deqing Hu; Yilin Zhou; Xuefeng Jiang
Journal:  Natl Sci Rev       Date:  2021-08-20       Impact factor: 23.178

  3 in total

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