Literature DB >> 24038907

Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium trifluoroacetate enabled by a flow system.

Mao Chen1, Stephen L Buchwald.   

Abstract

Going to the source: The trifluoromethylation of aryl/heteroaryl iodides has been demonstrated using a flow system, thus enabling a rapid rate of reaction. A broad spectrum of trifluoromethylated compounds was prepared in good to excellent yields using CF3 CO2 K as the trifluoromethyl source. The process has the advantage of short reaction times and uses convenient [CF3 ] sources.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; cross-coupling; flow chemistry; fluorine; synthetic methods

Mesh:

Substances:

Year:  2013        PMID: 24038907      PMCID: PMC3874851          DOI: 10.1002/anie.201306094

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


  46 in total

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Authors:  Lingling Chu; Feng-Ling Qing
Journal:  J Am Chem Soc       Date:  2011-12-21       Impact factor: 15.419

2.  On being green: can flow chemistry help?

Authors:  Steven V Ley
Journal:  Chem Rec       Date:  2012-06-18       Impact factor: 6.771

3.  Continuous flow coupling and decarboxylation reactions promoted by copper tubing.

Authors:  Yun Zhang; Timothy F Jamison; Sejal Patel; Nello Mainolfi
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4.  Transition-metal-catalyzed trifluoromethylation of aryl halides.

Authors:  Rylan J Lundgren; Mark Stradiotto
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

5.  Rapid and highly selective copper-free sonogashira coupling in high-pressure, high-temperature water in a microfluidic system.

Authors:  Hajime Kawanami; Keiichiro Matsushima; Masahiro Sato; Yutaka Ikushima
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6.  Ten key issues in modern flow chemistry.

Authors:  Jens Wegner; Sascha Ceylan; Andreas Kirschning
Journal:  Chem Commun (Camb)       Date:  2011-03-15       Impact factor: 6.222

7.  Continuous-flow synthesis of monoarylated acetaldehydes using aryldiazonium salts.

Authors:  Natalia Chernyak; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-07-19       Impact factor: 15.419

8.  Accessing Stereochemically Rich Sultams via Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS) Scale-out.

Authors:  Michael G Organ; Paul R Hanson; Alan Rolfe; Thiwanka B Samarakoon; Farman Ullah
Journal:  J Flow Chem       Date:  2011-08       Impact factor: 2.786

Review 9.  CF(3)-bearing aromatic and heterocyclic building blocks.

Authors:  Manfred Schlosser
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-18       Impact factor: 15.336

10.  Active trifluoromethylating agents from well-defined Copper(I)-CF3 complexes.

Authors:  Galyna G Dubinina; Hideki Furutachi; David A Vicic
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419

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  15 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.  Copper-Catalyzed Decarboxylative Trifluoromethylation of Propargyl Bromodifluoroacetates.

Authors:  Brett R Ambler; Santosh Peddi; Ryan A Altman
Journal:  Synthesis (Stuttg)       Date:  2014-07-15       Impact factor: 3.157

4.  Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale.

Authors:  Joel W Beatty; James J Douglas; Richard Miller; Rory C McAtee; Kevin P Cole; Corey R J Stephenson
Journal:  Chem       Date:  2016-09-08       Impact factor: 22.804

5.  Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

Authors:  Shi-Liang Shi; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-04       Impact factor: 15.336

6.  Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.

Authors:  Naish Lalloo; Christian A Malapit; S Maryamdokht Taimoory; Conor E Brigham; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2021-10-28       Impact factor: 15.419

7.  Difluoro-and Trifluoromethylation of Electron-Deficient Alkenes in an Electrochemical Microreactor.

Authors:  Kenta Arai; Kevin Watts; Thomas Wirth
Journal:  ChemistryOpen       Date:  2013-11-26       Impact factor: 2.911

8.  A scalable and operationally simple radical trifluoromethylation.

Authors:  Joel W Beatty; James J Douglas; Kevin P Cole; Corey R J Stephenson
Journal:  Nat Commun       Date:  2015-08-10       Impact factor: 14.919

9.  Regioselective synthesis of benzimidazolones via cascade C-N coupling of monosubstituted ureas.

Authors:  Johannes B Ernst; Nicholas E S Tay; Nathan T Jui; Stephen L Buchwald
Journal:  Org Lett       Date:  2014-06-27       Impact factor: 6.005

Review 10.  Carbon-carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations.

Authors:  Tsuyuka Sugiishi; Hideki Amii; Kohsuke Aikawa; Koichi Mikami
Journal:  Beilstein J Org Chem       Date:  2015-12-18       Impact factor: 2.883

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