Silver-Mediated Radical Trifluoromethylarylation of Activated Alkenes for the Synthesis of Oxindoles Bearing a CF3 Group

Wang, Yaofeng; Qiu, Jiashen; Kong, Dejie; Chen, Fuxue

doi:10.1055/s-0033-1341272

Cited by 20 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2014, Chen and co‐workers designed an effective protocol for the regioselectivity trifluoromethylarylation of oxindoles from N‐arylacrylamides (314) in presence of silver catalyst (Scheme 107). [214] This is an efficient method to prepare functionalized oxindoles containing CF 3 group (315) in good yields.…”

Section: Trifluoromethylation Reactionmentioning

confidence: 99%

Emergence of Ag as a Catalyst of Choice for Fluorination and Trifluoromethylation Reactions

2023

View full text Add to dashboard Cite

Carbon‐fluorine bond being highly polar in nature, its presence in pharmaceutically active molecules has huge impact on their chemical and physical properties. However, fluorine being highly electronegative and small in size, limits its nucleophilicity to the large extent; hence the incorporation of fluorine in the organic molecules is not an easy task. Due to this, demand for a suitable catalyst for fluorination reaction has been raised, which lowers the activation energy of these reactions and makes C−F/CF3 bond formation reaction kinetically more feasible. Silver being a late transition metal catalyst has been efficiently used to catalyze several reactions in the organic chemistry and has the substantial potential to catalyze the fluorination reactions. This Review shows the silver catalyzed fluorination and trifluoromethylation reactions for the synthesis of F/CF3 containing aromatic, aliphatic and heterocyclic compounds. All the sections have been elaborated using general discussion of the method, exploration of substrate scope, insight into the mechanistic studies and the shortcomings of the methods. After reading this Review article the readers can develop a detailed understanding of concept of silver metal catalyzed fluorination and trifluoromethylation reactions which can be explored for synthesizing molecules of biological interest.

show abstract

Section: Trifluoromethylation Reactionmentioning

confidence: 99%

Emergence of Ag as a Catalyst of Choice for Fluorination and Trifluoromethylation Reactions

2023

View full text Add to dashboard Cite

show abstract

“…Recently Quing group published aryloxydifluoromethylation and arylthiodifluoromethylation of heteroaromatic compounds by the silver(I) catalyzed decarboxylation of aryloxydifluoroacetic as well as arylthiodifluoroacetic acid (Scheme 12). [144] Through the similar strategy, silver(I) catalyzed oxidative radical addition and cyclization reactions of N-arylacrylamides with AgCF 3 (Chen, [145] Tan [146] ) or AgSCF 3 as well as nitrate ion-Scheme 10. Direct trifluoromethylation of arenes using trifluoroacetic acid and silver(I/II) as catalyst: (a) general conditions; (b) mechanism.…”

Section: Direct Formation Of C(sp 2 )à C(sp 3 ) Bondmentioning

confidence: 99%

“…Through the similar strategy, silver(I) catalyzed oxidative radical addition and cyclization reactions of N‐arylacrylamides with AgCF 3 (Chen, [145] Tan [146] ) or AgSCF 3 as well as nitrate ion‐Ag(I/0) (Wang [147] ) radical precursors have been successfully applied to the synthesis of the difunctionalization 3,3’‐substituted oxoindoles (Scheme 13).…”

Section: Silver In C−h Bond Functionalizationmentioning

confidence: 99%

Application of Silver Compounds in Fluoroorganic Synthesis: A Minireview

2023

View full text Add to dashboard Cite

The mini‐review is focused on application of silver and its compounds in fluoroorganic synthesis, and it reflects immense progress in this field which took place during the last two decades, with additional examples of reactivity of historical importance. Reactions of C−H, C−F, N−H and O−H bond functionalization, as well as catalysis of cycloaddition reactions and intramolecular rearrangement, retro‐rearrangement, and functional group migrations, have been described. Whenever available in original works, the reaction mechanisms were discussed. Since silver may be catalytically active in each of its available oxidation states from (0), via (I) and (II) to (III) with their immensely diverse properties, the organofluorine part is preceded by a brief overview of chemistry of silver in general. Uniqueness of silver among Group 11 elements is highlighted.

show abstract

“…First, some traditional processes will be discussed. [42,[45][46][47][48][49][50][51][52][53][54][55][56][57][58][59] Sodeoka and coworkers reported a simple and efficient method, which utilized Togni's reagent II and Cu(I) catalysis (Scheme 15). [46] Amongst transition-metal-free protocols, [51][52][53][54][55][56][57][58][59] Fu, Fu, Zou, and coworkers utilized Me 3 SiCF 3 in the presence of PhI(OAc) 2 oxidant, [51] Fu and coworkers applied CF 3 SO 2 Na and PhI(OAc) 2 oxidant, [52] while Wang and coworkers used CF 3 SO 2 Na and K 2 S 2 O 8 oxidant.…”

Section: Reactions Involving Intramolecular Cyclizationmentioning

confidence: 99%

Recent Progress in Aryltrifluoromethylation Reactions of Carbon‐Carbon Multiple Bonds

Remete

Nonn

Novák

et al. 2022

Chemistry An Asian Journal

View full text Add to dashboard Cite

Due to the increasing relevance of fluorinecontaining organic molecules in drug design, the synthesis of organofluorine compounds has gained high significance in synthetic organic chemistry. Trifluoromethylative difunctionalizations of carbon-carbon multiple bonds, with the simultaneous incorporation of a CF 3 group and another functional element, have considerable potential. Because of the high importance of carbon-carbon bond-forming reactions in organic synthesis, carbotrifluoromethylations and, in particular, aryltrifluoromethylations or heteroaryltrifluoromethylations are considered to be increasing fields of synthetic organic chemistry. The aim of the current review is to summarize recent developments of aryltrifluoromethylation or heteroaryltrifluoromethylation reactions.

show abstract

Silver-Mediated Radical Trifluoromethylarylation of Activated Alkenes for the Synthesis of Oxindoles Bearing a CF3 Group

Cited by 20 publications

References 0 publications

Emergence of Ag as a Catalyst of Choice for Fluorination and Trifluoromethylation Reactions

Emergence of Ag as a Catalyst of Choice for Fluorination and Trifluoromethylation Reactions

Application of Silver Compounds in Fluoroorganic Synthesis: A Minireview

Recent Progress in Aryltrifluoromethylation Reactions of Carbon‐Carbon Multiple Bonds

Contact Info

Product

Resources

About