Literature DB >> 28436132

Selective Aerobic Oxidation of Methylarenes to Benzaldehydes Catalyzed by N-Hydroxyphthalimide and Cobalt(II) Acetate in Hexafluoropropan-2-ol.

Eden Gaster1, Sebastian Kozuch1, Doron Pappo1.   

Abstract

Efficient and highly selective catalytic conditions for the aerobic autoxidation of methylarenes to benzaldehydes, based on N-hydroxyphthalimide (NHPI) and cobalt(II) acetate in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), were developed. The sustainable conditions enable a multigram scale preparation of benzaldehyde derivatives in high efficiency and with excellent chemoselectivity (up to 99 % conversion and 98 % selectivity).
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; aerobic oxidation; benzaldehydes; catalysis; solvent effects

Year:  2017        PMID： 28436132     DOI： 10.1002/anie.201702511

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


  13 in total

1.  Strain-Promoted Oxidation of Methylenecyclopropane Derivatives using N-Hydroxyphthalimide and Molecular Oxygen in the Dark.

Authors:  T E Anderson; K A Woerpel
Journal:  Org Lett       Date:  2020-07-09       Impact factor: 6.005

2.  Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors:  Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal:  Nat Rev Chem       Date:  2022-05-17       Impact factor: 34.571

3.  Electrochemical PINOylation of Methylarenes: Improving the Scope and Utility of Benzylic Oxidation through Mediated Electrolysis.

Authors:  Md Asmaul Hoque; Jack Twilton; Jieru Zhu; Matthew D Graaf; Kaid C Harper; Emilian Tuca; Gino A DiLabio; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2022-08-16       Impact factor: 16.383

4.  Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.

Authors:  Hai-Jun Zhang; Alexander W Schuppe; Shi-Tao Pan; Jin-Xiang Chen; Bo-Ran Wang; Timothy R Newhouse; Liang Yin
Journal:  J Am Chem Soc       Date:  2018-04-09       Impact factor: 15.419

5.  Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark.

Authors:  T E Anderson; Alexander A Andia; K A Woerpel
Journal:  Tetrahedron       Date:  2020-12-24       Impact factor: 2.457

6.  Resolving Oxygenation Pathways in Manganese-Catalyzed C(sp3)-H Functionalization via Radical and Cationic Intermediates.

Authors:  Marco Galeotti; Laia Vicens; Michela Salamone; Miquel Costas; Massimo Bietti
Journal:  J Am Chem Soc       Date:  2022-04-13       Impact factor: 16.383

7.  Chemoselective Aliphatic C-H Bond Oxidation Enabled by Polarity Reversal.

Authors:  Valeria Dantignana; Michela Milan; Olaf Cussó; Anna Company; Massimo Bietti; Miquel Costas
Journal:  ACS Cent Sci       Date:  2017-12-13       Impact factor: 14.553

8.  Electrosynthesis: A New Frontier in Aerobic Oxidation?

Authors:  Carlo Sambiagio; Hans Sterckx; Bert U W Maes
Journal:  ACS Cent Sci       Date:  2017-07-05       Impact factor: 14.553

9.  Bio-inspired iron-catalyzed oxidation of alkylarenes enables late-stage oxidation of complex methylarenes to arylaldehydes.

Authors:  Penghui Hu; Mingxi Tan; Lu Cheng; Hongyuan Zhao; Rui Feng; Wei-Jin Gu; Wei Han
Journal:  Nat Commun       Date:  2019-06-03       Impact factor: 14.919

Review 10.  Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622
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