Literature DB >> 21718039

Copper-catalyzed oxidative direct cyclization of N-methylanilines with electron-deficient alkenes using molecular oxygen.

Mayuko Nishino1, Koji Hirano, Tetsuya Satoh, Masahiro Miura.   

Abstract

The oxidative direct cyclizaion of N-methylanilines with electron-deficient alkenes involving maleimides and benzylidene malononitriles through sp(3) and sp(2) C-H bond cleavage proceeds effectively under a CuCl(2)/O(2) catalysis to provide the corresponding tetrahydroquinolines in good yields.

Entities:  

Year:  2011        PMID： 21718039     DOI： 10.1021/jo2011329

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Catalyst-free photoredox addition-cyclisations: exploitation of natural synergy between aryl acetic acids and maleimide.

Authors:  David W Manley; Andrew Mills; Christopher O'Rourke; Alexandra M Z Slawin; John C Walton
Journal:  Chemistry       Date:  2014-03-20       Impact factor: 5.236

3.  Eosin Y-catalyzed visible-light-mediated aerobic oxidative cyclization of N,N-dimethylanilines with maleimides.

Authors:  Zhongwei Liang; Song Xu; Wenyan Tian; Ronghua Zhang
Journal:  Beilstein J Org Chem       Date:  2015-04-01       Impact factor: 2.883

4.  Dual C-H functionalization of N-aryl amines: synthesis of polycyclic amines via an oxidative Povarov approach.

Authors:  Chang Min; Abbas Sanchawala; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-01       Impact factor: 6.005

5.  Photocatalytic reverse polarity Povarov reaction.

Authors:  Jamie A Leitch; Angel L Fuentes de Arriba; Joanne Tan; Oskar Hoff; Carlos M Martínez; Darren J Dixon
Journal:  Chem Sci       Date:  2018-07-06       Impact factor: 9.825

6.  Minimization of Back-Electron Transfer Enables the Elusive sp3 C-H Functionalization of Secondary Anilines.

Authors:  Huaibo Zhao; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-03       Impact factor: 15.336

7.  Borane-catalyzed cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines.

Authors:  Bei-Bei Zhang; Shuo Peng; Feiyi Wang; Cuifen Lu; Junqi Nie; Zuxing Chen; Guichun Yang; Chao Ma
Journal:  Chem Sci       Date:  2021-12-20       Impact factor: 9.825

8.  Aerobic Oxidative EDA Catalysis: Synthesis of Tetrahydroquinolines Using an Organocatalytic EDA Active Acceptor.

Authors:  August Runemark; Henrik Sundén
Journal:  J Org Chem       Date:  2022-01-10       Impact factor: 4.354

9.  Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine.

Authors:  Kun Wu; Zhiliang Huang; Xiaotian Qi; Yingzi Li; Guanghui Zhang; Chao Liu; Hong Yi; Lingkui Meng; Emilio E Bunel; Jeffrey T Miller; Chih-Wen Pao; Jyh-Fu Lee; Yu Lan; Aiwen Lei
Journal:  Sci Adv       Date:  2015-10-09       Impact factor: 14.136

10.  Oxidative Asymmetric Formal Aza-Diels⁻Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones.

Authors:  Xiang Wu; Shi-Bao Zhao; Lang-Lang Zheng; You-Gui Li
Journal:  Molecules       Date:  2018-09-01       Impact factor: 4.411
  10 in total

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