Literature DB >> 21827148

Silver-mediated trifluoromethoxylation of aryl stannanes and arylboronic acids.

Chenghong Huang1, Theresa Liang, Shinji Harada, Eunsung Lee, Tobias Ritter.   

Abstract

A silver-mediated cross-coupling of trifluoromethoxide with aryl stannanes and arylboronic acids to give aryl trifluoromethyl ethers is reported. This is the first report of a transition-metal-mediated C(aryl)-OCF(3) bond formation.

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Year:  2011        PMID： 21827148      PMCID： PMC3218431          DOI： 10.1021/ja204861a

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


  46 in total

1.  CF3 oxonium salts, O-(trifluoromethyl)dibenzofuranium salts: in situ synthesis, properties, and application as a real CF3+ species reagent.

Authors:  Teruo Umemoto; Kenji Adachi; Sumi Ishihara
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

Review 2.  Alpha-fluorinated ethers, thioethers, and amines: anomerically biased species.

Authors:  Frédéric Leroux; Peter Jeschke; Manfred Schlosser
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

3.  Facile Ar-CF3 bond formation at Pd. Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph].

Authors:  Vladimir V Grushin; William J Marshall
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

4.  Palladium-mediated fluorination of arylboronic acids.

Authors:  Takeru Furuya; Hanns Martin Kaiser; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Unexpected H2O-induced Ar-X activation with trifluoromethylpalladium(II) aryls.

Authors:  Vladimir V Grushin; William J Marshall
Journal:  J Am Chem Soc       Date:  2006-04-12       Impact factor: 15.419

6.  Pd-catalyzed synthesis of Ar-SCF3 compounds under mild conditions.

Authors:  Georgiy Teverovskiy; David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-20       Impact factor: 15.336

Review 7.  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

8.  Bimetallic palladium catalysis: direct observation of Pd(III)-Pd(III) intermediates.

Authors:  David C Powers; Matthias A L Geibel; Johannes E M N Klein; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

9.  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

10.  Trifluoromethyl ethers--synthesis and properties of an unusual substituent.

Authors:  Frédéric R Leroux; Baptiste Manteau; Jean-Pierre Vors; Sergiy Pazenok
Journal:  Beilstein J Org Chem       Date:  2008-04-29       Impact factor: 2.883
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  22 in total

1.  Silver-mediated trifluoromethylation of arenes using TMSCF3.

Authors:  Yingda Ye; Shin Hee Lee; Melanie S Sanford
Journal:  Org Lett       Date:  2011-09-20       Impact factor: 6.005

2.  Redox-Active Reagents for Photocatalytic Generation of the OCF3 Radical and (Hetero)Aryl C-H Trifluoromethoxylation.

Authors:  Weijia Zheng; Johnny W Lee; Cristian A Morales-Rivera; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-20       Impact factor: 15.336

3.  Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.

Authors:  Johnny W Lee; Sanghyun Lim; Daniel N Maienshein; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-24       Impact factor: 15.336

4.  Synthesis of Trifluoromethoxylated (Hetero)Arenes via OCF3 Migration.

Authors:  Katarzyna N Lee; Johnny W Lee; Ming-Yu Ngai
Journal:  Synlett       Date:  2015-11-16       Impact factor: 2.454

5.  Asymmetric silver-catalysed intermolecular bromotrifluoromethoxylation of alkenes with a new trifluoromethoxylation reagent.

Authors:  Shuo Guo; Fei Cong; Rui Guo; Liang Wang; Pingping Tang
Journal:  Nat Chem       Date:  2017-01-23       Impact factor: 24.427

6.  Catalytic C-H Trifluoromethoxylation of Arenes and Heteroarenes.

Authors:  Weijia Zheng; Cristian A Morales-Rivera; Johnny W Lee; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-13       Impact factor: 15.336

7.  Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives.

Authors:  Pengju Feng; Ming-Yu Ngai
Journal:  J Vis Exp       Date:  2016-01-19       Impact factor: 1.355

8.  Mild, Pd-catalyzed stannylation of radioiodination targets.

Authors:  Julie E Pickett; András Váradi; Travis C Palmer; Steven G Grinnell; Joel M Schrock; Gavril W Pasternak; Rashad R Karimov; Susruta Majumdar
Journal:  Bioorg Med Chem Lett       Date:  2015-03-02       Impact factor: 2.823

9.  Late-Stage Conversion of a Metabolically Labile Aryl Methyl Ether-Containing Natural Product to Fluoroalkyl Analogues.

Authors:  Jacob P Sorrentino; Brett R Ambler; Ryan A Altman
Journal:  J Org Chem       Date:  2020-03-27       Impact factor: 4.354

10.  Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration.

Authors:  Katarzyna N Lee; Zhen Lei; Cristian A Morales-Rivera; Peng Liu; Ming-Yu Ngai
Journal:  Org Biomol Chem       Date:  2016-06-15       Impact factor: 3.876
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