Literature DB >> 23931184

Use of fluoroform as a source of difluorocarbene in the synthesis of difluoromethoxy- and difluorothiomethoxyarenes.

Charles S Thomoson1, William R Dolbier.   

Abstract

Fluoroform, CHF3, a non-ozone-depleting, nontoxic, and inexpensive gas can be used as a difluorocarbene source in a process for the conversion of phenols and thiophenols to their difluoromethoxy and difluorothiomethoxy derivatives. The reactions are carried out at moderate temperatures and atmospheric pressure, using potassium hydroxide as base in a two-phase (water/dioxane or water/acetonitrile) process to provide moderate to good yields of the respective products.

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Year:  2013        PMID: 23931184     DOI: 10.1021/jo401392f

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  8 in total

Review 1.  Synthesis of Tri- and Difluoromethoxylated Compounds by Visible-Light Photoredox Catalysis.

Authors:  Johnny W Lee; Katarzyna N Lee; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-28       Impact factor: 15.336

2.  Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

Authors:  Conor E Brigham; Christian A Malapit; Naish Lalloo; Melanie S Sanford
Journal:  ACS Catal       Date:  2020-07-17       Impact factor: 13.084

3.  Conversion of Methyl Ketones and Methyl Sulfones into α-Deutero-α,α-Difluoromethyl Ketones and α-Deutero-α,α-Difluoromethyl Sulfones in Three Synthetic Steps.

Authors:  Munia F Sowaileh; Changho Han; Robert A Hazlitt; Eun Hoo Kim; Jinu P John; David A Colby
Journal:  Tetrahedron Lett       Date:  2016-12-21       Impact factor: 2.415

Review 4.  Repurposing of F-gases: challenges and opportunities in fluorine chemistry.

Authors:  Daniel J Sheldon; Mark R Crimmin
Journal:  Chem Soc Rev       Date:  2022-06-20       Impact factor: 60.615

5.  19F-NMR Diastereotopic Signals in Two N-CHF₂ Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole.

Authors:  Diana García-Pérez; Concepción López; Rosa M Claramunt; Ibon Alkorta; José Elguero
Journal:  Molecules       Date:  2017-11-17       Impact factor: 4.411

6.  Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N-Sulfinylimines.

Authors:  Kazuki Hirano; Satoshi Gondo; Nagender Punna; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2019-02-05       Impact factor: 2.911

Review 7.  Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C-C Bonds.

Authors:  Sebastián Barata-Vallejo; Al Postigo
Journal:  Molecules       Date:  2019-12-06       Impact factor: 4.411

8.  Radical difluoromethylthiolation of aromatics enabled by visible light.

Authors:  Jianbin Li; Dianhu Zhu; Leiyang Lv; Chao-Jun Li
Journal:  Chem Sci       Date:  2018-06-01       Impact factor: 9.825

  8 in total

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