Literature DB >> 27782348

(C6 F5 )3 B Catalyzed Chemoselective and ortho-Selective Substitution of Phenols with α-Aryl α-Diazoesters.

Zhunzhun Yu1, Yongfeng Li1, Jiameng Shi2, Ben Ma1, Lu Liu1, Junliang Zhang1.   

Abstract

The development of an efficient method for the site-selective substitution of unprotected phenols has long been considered as an attractive but challenging task. Herein, we describe a highly chemo- and ortho-selective substitution reaction of phenols with α-aryl α-diazoacetates with commercially available (C6 F5 )3 B as the catalyst. This reaction proceeds under simple and mild conditions with high efficiency, it features a wide substrate scope and can be easily scaled up.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H functionalization; boron catalysis; chemoselectivity; diazo compounds; phenols

Year:  2016        PMID: 27782348     DOI: 10.1002/anie.201608937

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


  6 in total

1.  Overcoming O-H Insertion to Para-Selective C-H Functionalization of Free Phenols: Rh(II)/Xantphos Catalyzed Geminal Difunctionalization of Diazo Compounds.

Authors:  Yang Yang; Bin Lu; Guiqing Xu; Xiaoming Wang
Journal:  ACS Cent Sci       Date:  2022-04-20       Impact factor: 18.728

2.  Rapid Synthesis of N-Tosylhydrazones under Solvent-Free Conditions and Their Potential Application Against Human Triple-Negative Breast Cancer.

Authors:  Zengyang Xie; Yuying Song; Lujia Xu; Yukun Guo; Min Zhang; Limei Li; Kai Chen; Xue Liu
Journal:  ChemistryOpen       Date:  2018-11-21       Impact factor: 2.911

Review 3.  Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors.

Authors:  Ayan Dasgupta; Emma Richards; Rebecca L Melen
Journal:  ACS Catal       Date:  2021-12-17       Impact factor: 13.084

4.  Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens.

Authors:  Xun-Shen Liu; Zhiqiong Tang; Zhiming Li; Mingjia Li; Lin Xu; Lu Liu
Journal:  Nat Commun       Date:  2021-12-15       Impact factor: 14.919

5.  DFT Mechanistic Study of the Cyclopropanation of Styrene and Aryldiazodiacetate Catalyzed by Tris(pentafluorophenyl)borane.

Authors:  Xiuling Wen; Peiquan Lu; Yong Shen; Haojie Peng; Zhuofeng Ke; Cunyuan Zhao
Journal:  ACS Omega       Date:  2022-04-07

6.  Understanding the Influence of Donor-Acceptor Diazo Compounds on the Catalyst Efficiency of B(C6 F5 )3 Towards Carbene Formation.

Authors:  Rasool Babaahmadi; Ayan Dasgupta; Christopher J T Hyland; Brian F Yates; Rebecca L Melen; Alireza Ariafard
Journal:  Chemistry       Date:  2022-01-27       Impact factor: 5.020

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.