Literature DB >> 22984900

Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).

Yingda Ye1, Stefan A Künzi, Melanie S Sanford.   

Abstract

A mild and practical protocol for the copper-mediated trifluoromethylation of aryl and heteroaryl boronic acids using NaSO(2)CF(3) (Langlois' reagent) and TBHP is described. The reaction proceeds at room temperature under ambient conditions, and the products can be readily purified by extraction or column chromatography.

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Year:  2012        PMID： 22984900      PMCID： PMC3513340          DOI： 10.1021/ol3022726

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


  27 in total

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2.  Copper-mediated oxidative trifluoromethylation of boronic acids.

Authors:  Lingling Chu; Feng-Ling Qing
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3.  Photoredox catalysis: a mild, operationally simple approach to the synthesis of α-trifluoromethyl carbonyl compounds.

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Authors:  Nichole D Litvinas; Patrick S Fier; John F Hartwig
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5.  Oxidative trifluoromethylation of arylboronates with shelf-stable potassium (trifluoromethyl)trimethoxyborate.

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Journal:  Chemistry       Date:  2012-01-11       Impact factor: 5.236

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7.  Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent.

Authors:  Jun Xu; Dong-Fen Luo; Bin Xiao; Zhao-Jing Liu; Tian-Jun Gong; Yao Fu; Lei Liu
Journal:  Chem Commun (Camb)       Date:  2011-03-07       Impact factor: 6.222

8.  Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent.

Authors:  Tianfei Liu; Qilong Shen
Journal:  Org Lett       Date:  2011-04-07       Impact factor: 6.005

9.  Copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids using (trifluoromethyl)trimethylsilane.

Authors:  Xueliang Jiang; Lingling Chu; Feng-Ling Qing
Journal:  J Org Chem       Date:  2012-01-20       Impact factor: 4.354

Review 10.  CF(3)-bearing aromatic and heterocyclic building blocks.

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2.  Copper-mediated radical trifluoromethylation of unsaturated potassium organotrifluoroborates.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  J Org Chem       Date:  2013-11-19       Impact factor: 4.354

3.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

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4.  Laser-Initiated Radical Trifluoromethylation of Peptides and Proteins: Application to Mass-Spectrometry-Based Protein Footprinting.

Authors:  Ming Cheng; Bojie Zhang; Weidong Cui; Michael L Gross
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Review 5.  Solar synthesis: prospects in visible light photocatalysis.

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6.  Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.

Authors:  Ryan Gianatassio; Shuhei Kawamura; Cecil L Eprile; Klement Foo; Jason Ge; Aaron C Burns; Michael R Collins; Phil S Baran
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7.  Direct synthesis of fluorinated heteroarylether bioisosteres.

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8.  Trifluoromethylation of Heterocycles in Water at Room Temperature.

Authors:  James C Fennewald; Bruce H Lipshutz
Journal:  Green Chem       Date:  2014-03-01       Impact factor: 10.182

9.  Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ].

Authors:  Johannes Morstein; Haiyun Hou; Chen Cheng; John F Hartwig
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10.  Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations.

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Journal:  Chem Sci       Date:  2021-04-26       Impact factor: 9.825
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