Literature DB >> 24059700

S-, N-, and Se-difluoromethylation using sodium chlorodifluoroacetate.

Vaibhav P Mehta1, Michael F Greaney.   

Abstract

A simple protocol for the difluoromethylation of thiols is reported using chlorodifluoroacetate as the difluoromethylating agent. This cheap reagent undergoes smooth decarboxylation at 95 °C to afford difluorocarbene, which can be trapped with a variety of aromatic and heteroaromatic thiols. The reaction is also effective for the difluoromethylation of heterocyclic nitrogen compounds and phenylselenol.

Entities:  

Year:  2013        PMID: 24059700     DOI: 10.1021/ol402370f

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  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

Review 2.  Decarboxylative fluorination strategies for accessing medicinally- relevant products.

Authors:  Yupu Qiao; Lingui Zhu; Brett R Ambler; Ryan A Altman
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

3.  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

Review 4.  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

5.  Synthesis of purines and adenines containing the hexafluoroisopropyl group.

Authors:  Viacheslav Petrov; Rebecca J Dooley; Alexander A Marchione; Brittany S Clem; William Marshall; Elizabeth L Diaz
Journal:  Beilstein J Org Chem       Date:  2020-11-11       Impact factor: 2.883

6.  Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis.

Authors:  Sadayuki Arimori; Okiya Matsubara; Masahiro Takada; Motoo Shiro; Norio Shibata
Journal:  R Soc Open Sci       Date:  2016-05-25       Impact factor: 2.963

7.  Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides.

Authors:  Jiang Wu; Yafei Liu; Changhui Lu; Qilong Shen
Journal:  Chem Sci       Date:  2016-02-17       Impact factor: 9.825

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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