Literature DB >> 22715116

Fluoroform-derived CuCF3 for low-cost, simple, efficient, and safe trifluoromethylation of aryl boronic acids in air.

Petr Novák1, Anton Lishchynskyi, Vladimir V Grushin.   

Abstract

Easy does it: Aryl boronic acids undergo smooth and selective trifluoromethylation with low-cost fluoroform-derived CuCF(3) in DMF in non-dried air. The reaction occurs under mild conditions (1 atm, room temperature), exhibits unprecedented functional-group tolerance, and affords trifluoromethylated aromatic compounds in up to 99 % yield.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22715116     DOI： 10.1002/anie.201201613

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


  14 in total

1.  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

2.  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

Review 3.  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

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

Authors:  Yingda Ye; Stefan A Künzi; Melanie S Sanford
Journal:  Org Lett       Date:  2012-09-17       Impact factor: 6.005

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

Authors:  Mao Chen; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-05       Impact factor: 15.336

6.  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

7.  Direct nucleophilic trifluoromethylation of carbonyl compounds by potent greenhouse gas, fluoroform: Improving the reactivity of anionoid trifluoromethyl species in glymes.

Authors:  Takuya Saito; Jiandong Wang; Etsuko Tokunaga; Seiji Tsuzuki; Norio Shibata
Journal:  Sci Rep       Date:  2018-07-31       Impact factor: 4.379

8.  Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations.

Authors:  Shengjia Lin; Lucia Wang; Abhishek Sharma
Journal:  Chem Sci       Date:  2021-04-26       Impact factor: 9.825

9.  Organocatalyzed Trifluoromethylation of Ketones and Sulfonyl Fluorides by Fluoroform under a Superbase System.

Authors:  Satoshi Okusu; Kazuki Hirano; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2015-08-06       Impact factor: 2.911

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
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.