Literature DB >> 33690769

Installing the "magic methyl"- C-H methylation in synthesis.

Daniya Aynetdinova1, Mia C Callens, Harry B Hicks, Charmaine Y X Poh, Benjamin D A Shennan, Alistair M Boyd, Zhong Hui Lim, Jamie A Leitch, Darren J Dixon.   

Abstract

The selective and efficient C-H methylation of sp2 and sp3 carbon centres has become a powerful transformation in the synthetic toolbox. Due to the potential for profound changes to physicochemical properties attributed to the installation of a "Magic Methyl" group at a strategic site in a lead compound, such techniques have become highly desirable in modern drug discovery and synthesis programmes. This review will cover the diverse techniques that have been employed to enable the selective installation of the C-Me bond in a wide range of chemical structures, from simple building blocks to complex drug-like architectures.

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Year:  2021        PMID: 33690769     DOI: 10.1039/d0cs00973c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  12 in total

1.  Site-Selective α-C-H Functionalization of Trialkylamines via Reversible Hydrogen Atom Transfer Catalysis.

Authors:  Yangyang Shen; Ignacio Funez-Ardoiz; Franziska Schoenebeck; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-11-05       Impact factor: 15.419

2.  Structural Basis for Control of Methylation Extent in Polyketide Synthase Metal-Dependent C-Methyltransferases.

Authors:  Yongtong Lao; Meredith A Skiba; Stephanie W Chun; Alison R H Narayan; Janet L Smith
Journal:  ACS Chem Biol       Date:  2022-05-20       Impact factor: 4.634

3.  C(sp3)-H methylation enabled by peroxide photosensitization and Ni-mediated radical coupling.

Authors:  Aristidis Vasilopoulos; Shane W Krska; Shannon S Stahl
Journal:  Science       Date:  2021-04-23       Impact factor: 47.728

4.  Modifications of the Triaminoaryl Metabophore of Flupirtine and Retigabine Aimed at Avoiding Quinone Diimine Formation.

Authors:  Konrad W Wurm; Frieda-Marie Bartz; Lukas Schulig; Anja Bodtke; Patrick J Bednarski; Andreas Link
Journal:  ACS Omega       Date:  2022-02-25

5.  Selective α-Methylation of Aryl Ketones Using Quaternary Ammonium Salts as Solid Methylating Agents.

Authors:  Johanna Templ; Michael Schnürch
Journal:  J Org Chem       Date:  2022-03-07       Impact factor: 4.354

6.  Rhodium-Catalyzed C-H Methylation and Alkylation Reactions by Carbene-Transfer Reactions.

Authors:  Claire Empel; Sripati Jana; Tim Langletz; Rene M Koenigs
Journal:  Chemistry       Date:  2022-02-02       Impact factor: 5.020

7.  Rhoda-Electrocatalyzed C-H Methylation and Paired Electrocatalyzed C-H Ethylation and Propylation.

Authors:  Krzysztof Kuciński; Hendrik Simon; Lutz Ackermann
Journal:  Chemistry       Date:  2021-11-10       Impact factor: 5.020

8.  Scalable (Enantioselective) Syntheses of Novel 3-Methylated Analogs of Pazinaclone, (S)-PD172938 and Related Biologically Relevant Isoindolinones.

Authors:  Antonia Di Mola; Giorgia Nicastro; Lorenzo Serusi; Rosanna Filosa; Mario Waser; Antonio Massa
Journal:  Molecules       Date:  2022-09-01       Impact factor: 4.927

9.  Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds.

Authors:  Xi Yang; Gang Wang; Zhi-Shi Ye
Journal:  Chem Sci       Date:  2022-08-18       Impact factor: 9.969

10.  A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes.

Authors:  Eduardo de Pedro Beato; Davide Spinnato; Wei Zhou; Paolo Melchiorre
Journal:  J Am Chem Soc       Date:  2021-07-28       Impact factor: 15.419

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