Literature DB >> 16847982

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

Manfred Schlosser1.   

Abstract

Fluorine remains an insiders' tip in the life sciences as it enables the fine-tuning of biological properties. However, the synthesis of fluorine-substituted target compounds is not always trivial. Virtually any fluorine atom attached to an organic backbone has ultimately to be imported from inorganic sources. Crucial for the entire synthetic planning in medicinal and agricultural research is the decision on at what stage and how the halogen will be introduced. Standard technical processes, in particular the displacement of chlorine using anhydrous hydrogen fluoride or potassium fluoride, can hardly be implemented rationally on the laboratory scale. Universal methods that are applicable by both industrial and academic researchers thus have great appeal. If a trifluoromethyl-substituted arene or heterocycle is the target compound, two splendid options exist. The CF(3) group can be delivered packagewise by coupling an appropriate substrate with in situ generated (trifluoromethyl)copper. Alternatively, one may start from a CF(3)-substituted arene or heterocycle as a core and complete it with the missing parts of the ultimate structure.

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Year:  2006        PMID: 16847982     DOI: 10.1002/anie.200600449

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


  25 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.  Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I.

Authors:  Yingda Ye; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419

3.  Investigations into Transition Metal Catalyzed Arene Trifluoromethylation Reactions.

Authors:  Yingda Ye; Melanie S Sanford
Journal:  Synlett       Date:  2012-09-01       Impact factor: 2.454

4.  Copper-catalyzed oxytrifluoromethylation of unactivated alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

5.  Trifluoromethylation of Secondary Nitroalkanes.

Authors:  Amber A S Gietter-Burch; Vijayarajan Devannah; Donald A Watson
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

6.  Silver-mediated trifluoromethoxylation of aryl stannanes and arylboronic acids.

Authors:  Chenghong Huang; Theresa Liang; Shinji Harada; Eunsung Lee; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2011-08-09       Impact factor: 15.419

7.  Copper-catalyzed arylation of 1H-perfluoroalkanes.

Authors:  Ilya Popov; Sergey Lindeman; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-05-31       Impact factor: 15.419

8.  Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

Authors:  Gary A Molander; Livia N Cavalcanti; Carolina García-García
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

9.  Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates.

Authors:  Brett R Ambler; Lingui Zhu; Ryan A Altman
Journal:  J Org Chem       Date:  2015-08-11       Impact factor: 4.354

10.  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

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