Literature DB >> 31736186

Green Metal-Free Photochemical Hydroacylation of Unactivated Olefins.

Errika Voutyritsa1, Christoforos G Kokotos1.   

Abstract

Direct alkylation of C(sp2 )-H bonds to convert an aldehyde into a ketone is a notorious transformation, due to the laborious challenge of the formation of ketyl or acyl radicals. Herein, we report a green, cheap, metal-free and efficient method for the hydroacylation of olefins in water. This photochemical protocol utilizes phenylglyoxylic acid, a commercially available small organic molecule, as the photoinitiator, water as the solvent and household fluorescent lamps as the irradiation source, leading to a broad substrate scope of products in moderate to good yields. A wide range of aromatic and aliphatic aldehydes, terminal and non-terminal alkenes and pharmaceutically relevant molecules can be employed, without the need of directing groups and additives or metal catalysts.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; aldehydes; green chemistry; olefins; photochemistry

Year:  2019        PMID: 31736186     DOI: 10.1002/anie.201912214

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


  6 in total

1.  Photochemical C-H acetalization of O-heterocycles utilizing phenylglyoxylic acid as the photoinitiator.

Authors:  Giorgos S Koutoulogenis; Nikoleta Spiliopoulou; Christoforos G Kokotos
Journal:  Photochem Photobiol Sci       Date:  2021-11-09       Impact factor: 4.328

2.  Photomediated reductive coupling of nitroarenes with aldehydes for amide synthesis.

Authors:  Qingyao Li; Peng Dai; Haidi Tang; Muliang Zhang; Jie Wu
Journal:  Chem Sci       Date:  2022-08-03       Impact factor: 9.969

3.  Synthesis of New Morphinan Opioids by TBADT-Catalyzed Photochemical Functionalization at the Carbon Skeleton.

Authors:  Dmitry Gorbachev; Elliot Smith; Stephen P Argent; Graham N Newton; Hon Wai Lam
Journal:  Chemistry       Date:  2022-07-13       Impact factor: 5.020

4.  Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls.

Authors:  Shengfei Jin; Hang T Dang; Graham C Haug; Viet D Nguyen; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2020-07-01       Impact factor: 9.825

5.  Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light.

Authors:  Andrea Serafino; Davide Balestri; Luciano Marchiò; Max Malacria; Etienne Derat; Giovanni Maestri
Journal:  Org Lett       Date:  2020-08-05       Impact factor: 6.005

Review 6.  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

  6 in total

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