Literature DB >> 15563143

Direct access to ketones from aldehydes via rhodium-catalyzed cross-coupling reaction with potassium trifluoro(organo)borates.

Mathieu Pucheault1, Sylvain Darses, Jean-Pierre Genet.   

Abstract

A direct cross-coupling reaction of aromatic aldehydes with potassium trifluoro(organo)borates afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst and acetone. This new reaction, involving a formal aldehyde C-H bond activation, is believed to proceed via a Heck-type mechanism followed by hydride transfer to acetone.

Entities:  

Year:  2004        PMID: 15563143     DOI: 10.1021/ja044749b

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

2.  Aryl ketone synthesis via tandem orthoplatinated triarylphosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation.

Authors:  Yuan-Xi Liao; Qiao-Sheng Hu
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

Review 3.  Benzophenone: a ubiquitous scaffold in medicinal chemistry.

Authors:  Khemchand Surana; Bharatkumar Chaudhary; Monika Diwaker; Satyasheel Sharma
Journal:  Medchemcomm       Date:  2018-08-23       Impact factor: 3.597

4.  Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.

Authors:  Baris Yucel; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-11-24       Impact factor: 5.837

5.  Iterative Cross-Couplng with MIDA Boronates: Towards a General Platform for Small Molecule Synthesis.

Authors:  Eric P Gillis; Martin D Burke
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

6.  Synthesis of Cyclohexanones by a Tandem Photocatalyzed Annulation.

Authors:  Anna V Bay; Emelia J Farnam; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2022-03-22       Impact factor: 16.383

7.  (1)H, (13)C, (19)F and (11)B NMR spectral reference data of some potassium organotrifluoroborates.

Authors:  Roberta A Oliveira; Ricardo O Silva; Gary A Molander; Paulo H Menezes
Journal:  Magn Reson Chem       Date:  2009-10       Impact factor: 2.447

8.  Multistep synthesis of complex boronic acids from simple MIDA boronates.

Authors:  Eric P Gillis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2008-10-07       Impact factor: 15.419

9.  Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors:  Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

  9 in total

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