Literature DB >> 26212483

Palladium-Catalyzed Hydroamidocarbonylation of Olefins to Imides.

Haoquan Li1, Kaiwu Dong1, Helfried Neumann1, Matthias Beller2.   

Abstract

Carbonylation reactions allow the efficient synthesis of all kinds of carbonyl-containing compounds. Here, we report a straightforward synthesis of various imides from olefins and CO for the first time. The established hydroamidocarbonylation reaction affords imides in good yields (up to 90 %) and with good regioselectivity (up to 99:1) when applying different alkenes and amides. The synthetic potential of the method is highlighted by the synthesis of Aniracetam by intramolecular hydroamidocarbonylation.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; amides; carbonylation; homogeneous catalysis; imides

Year:  2015        PMID: 26212483     DOI: 10.1002/anie.201503954

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


  6 in total

1.  Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins.

Authors:  Jiefeng Hu; Minyan Wang; Xinghui Pu; Zhuangzhi Shi
Journal:  Nat Commun       Date:  2017-05-05       Impact factor: 14.919

2.  Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride.

Authors:  Bao Gao; Guoying Zhang; Xibing Zhou; Hanmin Huang
Journal:  Chem Sci       Date:  2017-10-24       Impact factor: 9.825

3.  CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides.

Authors:  Kengo Kataoka; Keiju Wachi; Xiongjie Jin; Kosuke Suzuki; Yusuke Sasano; Yoshiharu Iwabuchi; Jun-Ya Hasegawa; Noritaka Mizuno; Kazuya Yamaguchi
Journal:  Chem Sci       Date:  2018-05-07       Impact factor: 9.825

4.  Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones.

Authors:  Yao Ge; Fei Ye; Jiawang Liu; Ji Yang; Anke Spannenberg; Haijun Jiao; Ralf Jackstell; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-17       Impact factor: 15.336

5.  Metal-free photoredox-catalyzed direct α-oxygenation of N,N-dibenzylanilines to imides under visible light.

Authors:  Nalladhambi Neerathilingam; Ramasamy Anandhan
Journal:  RSC Adv       Date:  2022-03-15       Impact factor: 3.361

6.  Toward Green Acylation of (Hetero)arenes: Palladium-Catalyzed Carbonylation of Olefins to Ketones.

Authors:  Jie Liu; Zhihong Wei; Haijun Jiao; Ralf Jackstell; Matthias Beller
Journal:  ACS Cent Sci       Date:  2017-11-16       Impact factor: 14.553

  6 in total

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