Literature DB >> 29604154

Redox-Divergent Synthesis of Fluoroalkylated Pyridines and 2-Pyridones through Cu-Catalyzed N-O Cleavage of Oxime Acetates.

Dachang Bai1, Xueli Wang2, Guangfan Zheng2, Xingwei Li1,2.   

Abstract

Cu-catalyzed redox-divergent [3+3] coupling of oxime esters with β-CF3 enones and acrylates is described. This redox-neutral coupling with enones and acrylates affords trifluoromethylated pyridines and pyridones, respectively. Under reductive conditions, difluoromethylated pyridines, difluoromethlated pyridones, and trifluoromethylated dihydropyridones are obtained. The reactions occur under mild conditions with broad substrate scope and regio/redox selectivity.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; fluoroalkylation; oximes; pyridines; pyridones

Year:  2018        PMID： 29604154     DOI： 10.1002/anie.201802311

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


  5 in total

1.  Iminyl radical-triggered relay annulation for the construction of bridged aza-tetracycles bearing four contiguous stereogenic centers.

Authors:  Kun Jiang; Shi-Jun Li; Qing-Peng Liu; Ning Yu; Yu-Lin Li; Yu-Qiang Zhou; Kui-Cheng He; Jing Lin; Ting-Yu Zheng; Jian Lang; Yu Lan; Ye Wei
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

2.  Switching the Regioselectivity Access to Pyrroles and Isoquinolines from Ketoxime Acetates and Ynals.

Authors:  Tanggao Liu; Fan Xu; Xiaojuan Liu; Zhiqing Huang; Lipeng Long; Guohai Xu; Hong Xiao; Zhengwang Chen
Journal:  ACS Omega       Date:  2020-11-23

3.  Facile synthesis of 6-organyl-4-(trifluoromethyl)pyridin-2(1H)-ones and their polyfluoroalkyl-containing analogs.

Authors:  S O Kushch; M V Goryaeva; Ya V Burgart; G A Triandafilova; K O Malysheva; O P Krasnykh; N A Gerasimova; N P Evstigneeva; V I Saloutin
Journal:  Russ Chem Bull       Date:  2022-09-23       Impact factor: 1.704

4.  Practical Synthesis of α-Trifluoromethylated Pyridines Based on Regioselective Cobalt-Catalyzed [2+2+2] Cycloaddition using Trifluoromethylated Diynes with Nitriles.

Authors:  Tatsuya Kumon; Shigeyuki Yamada; Tomohiro Agou; Hiroki Fukumoto; Toshio Kubota; Gerald B Hammond; Tsutomu Konno
Journal:  Adv Synth Catal       Date:  2021-01-22       Impact factor: 5.837

5.  Rhodium(i)-catalyzed C6-selective C-H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids.

Authors:  Haoqiang Zhao; Xin Xu; Zhenli Luo; Lei Cao; Bohan Li; Huanrong Li; Lijin Xu; Qinghua Fan; Patrick J Walsh
Journal:  Chem Sci       Date:  2019-09-09       Impact factor: 9.825
  5 in total

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