Copper-Promoted Sandmeyer Trifluoromethylation Reaction

Dai, Jianjun; Feng, Cheng; Xiao, Bin; Yi, Jun; Xu, Jun; Liu, Zhao‐Jing; Lü, Xi; Liu, Lei; Fu, Yao

doi:10.1021/ja404217t

Cited by 267 publications

(89 citation statements)

References 72 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Two synthetic protocols have been recently described to perform this transformation, consisting in the reaction of the derived diazonium salts with Umemoto's reagent and Cu metal [27], or with CF 3 SiMe 3 and AgF [28] (Scheme 1, path d).…”

Section: Trifluoromethylation Of Aromatic Compoundsmentioning

confidence: 99%

Recent advances in the trifluoromethylation methodology and new CF3-containing drugs

Zhu

Wang

et al. 2014

Journal of Fluorine Chemistry

410

209

View full text Add to dashboard Cite

Section: Trifluoromethylation Of Aromatic Compoundsmentioning

confidence: 99%

Recent advances in the trifluoromethylation methodology and new CF3-containing drugs

Zhu

Wang

et al. 2014

Journal of Fluorine Chemistry

410

209

View full text Add to dashboard Cite

“…Among all fluorine-containing moieties, the trifluoromethyl group is privileged4, and trifluoromethylated arenes are of interest for agrochemicals, pharmaceuticals and advanced materials5. Several excellent methods to provide structurally diverse CF 3 -building blocks have been elaborated678: common strategies to introduce the CF 3 -group into aromatic compounds involve metal-mediated/catalysed functional group interconversions910 where halogens111213, boronic acids141516, boronates1718 and even amines1920 are replaced by nucleophilic, electrophilic or radical CF 3 -sources (Fig. 1a).…”

mentioning

confidence: 99%

Biocatalytic trifluoromethylation of unprotected phenols

et al. 2016

View full text Add to dashboard Cite

Organofluorine compounds have become important building blocks for a broad range of advanced materials, polymers, agrochemicals, and increasingly for pharmaceuticals. Despite tremendous progress within the area of fluorination chemistry, methods for the direct introduction of fluoroalkyl-groups into organic molecules without prefunctionalization are still highly desired. Here we present a concept for the introduction of the trifluoromethyl group into unprotected phenols by employing a biocatalyst (laccase), tBuOOH, and either the Langlois' reagent or Baran's zinc sulfinate. The method relies on the recombination of two radical species, namely, the phenol radical cation generated directly by the laccase and the CF3-radical. Various functional groups such as ketone, ester, aldehyde, ether and nitrile are tolerated. This laccase-catalysed trifluoromethylation proceeds under mild conditions and allows accessing trifluoromethyl-substituted phenols that were not available by classical methods.

show abstract

“…After this, he was awarded with a Marie Curie fellowship to work in Würzburg (Germany) with Prof. Helmut Werner. [20][21][22][23][24][25][26][27] Most metal-promoted synthetic routes for trifluoromethylated organic compounds make use of copper trifluoromethyl complexes, 22,24,26,[28][29][30][31] some of which were used as trifluoromethylating agents in organic synthesis for a long time. His main research interests include the study of new reactions of fluorinated organometallic complexes of the platinum-group metals and gold, and the study of self-assembly processes involving organometallic and coordination complexes.…”

Section: And They Offer Industrial Applications As Advancedmentioning

confidence: 99%

Gold trifluoromethyl complexes

Gil‐Rubio

Vicente

2015

Dalton Trans.

View full text Add to dashboard Cite

This article reviews the synthesis, reactivity and applications of gold trifluoromethyl complexes, which are the only isolated perfluoroalkyl complexes of gold. The most reported examples are neutral Au(i) complexes of the type [Au(CF3)L], whereas only two Au(ii) trifluoromethyl complexes have been reported, both being diamagnetic and containing a strong Au-Au bond. A number of Au(iii) trifluoromethyl complexes have been prepared by oxidative addition of halogens or iodotrifluoromethane to Au(i) complexes or, in a few cases, by transmetallation reactions. Owing to the limitations of the available synthetic methods, a lower number of examples is known, particularly for the oxidation states (ii) and (iii). Gold trifluoromethyl complexes present singular characteristics, such as thermal stability, strong Au-C bonds and, in some cases, reactive α-C-F bonds. Some of the Au(iii) complexes reported, show unusually easy reductive elimination reactions of trifluoromethylated products which could be applied in the development of gold-catalyzed processes for the trifluoromethylation of organic compounds.

show abstract

Copper-Promoted Sandmeyer Trifluoromethylation Reaction

Cited by 267 publications

References 72 publications

Recent advances in the trifluoromethylation methodology and new CF3-containing drugs

Recent advances in the trifluoromethylation methodology and new CF3-containing drugs

Biocatalytic trifluoromethylation of unprotected phenols

Gold trifluoromethyl complexes

Contact Info

Product

Resources

About