Fluoroform: an Efficient Precursor for the Trifluoromethylation of Aldehydes

Folléas, Benoît; Marek, Ilan; Normant, Jean F.; Jalmes, Laurent Saint

doi:10.1016/s0040-4020(99)00951-5

Cited by 119 publications

(89 citation statements)

References 57 publications

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“…26,[31][32][33][34] A series of aldehydes and ketones were tested for trifluoromethylation, and gave moderate to good yields of the target products 2 in most cases. 24,[35][36][37] In these studies, various carbonyl compounds were scrutinized, giving moderate to good yields of products 2, 4 or 5 in most cases.…”

Section: Trifluoromethylation or Difluoromethylation Of Carbonyl Compmentioning

confidence: 99%

Application of fluoroform in trifluoromethylation and diﬂuoromethylation reactions

Zhang¹

2017

Arkivoc

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Recent development in the trifluoromethylation and difluoromethylation of organic compounds employing fluoroform is reviewed. Eight approaches to trifluoromethylation and difluoromethylation are summarized: (i) trifluoromethylation or difluoromethylation of carbonyl compounds, (ii) trifluoromethylation of sulfonyl fluorides, (iii) trifluoromethylation of epoxides, (iv) nucleophilic trifluoromethylation of silicon, boron, and sulfur-based compounds, (v) CuCF3 derived from fluoroform for the trifluoromethylation of aryl or heteroaryl halides, aryl boronic acids, arenediazonium salts and alkynes, (vi) difluoromethylation of alkynes, (vii) difluoromethylation of phenols, thiophenols and heterocyclic compounds, and (viii) difluoromethylation of nitriles.

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Section: Trifluoromethylation or Difluoromethylation Of Carbonyl Compmentioning

confidence: 99%

Application of fluoroform in trifluoromethylation and diﬂuoromethylation reactions

Zhang¹

2017

Arkivoc

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“…[17] Trifluoromethyllithium, [18] unlike, for example, dibromofluoromethyllithium, [19] is unstable even at extremely low temperatures owing to instantaneously ensuing elimination and substitution reactions. On the other hand, trifluoromethanide (trifluoromethyl anion) can be readily generated from (trifluoromethyl)trimethylsilane [20] or trifluoromethane (fluoroform) [21] and trapped in situ. Under such conditions, of Fluorine remains an insiders tip in the life sciences as it enables the fine-tuning of biological properties.…”

Section: Copper-mediated Iodo/trifluoromethyl Displacementmentioning

confidence: 99%

CF₃‐Bearing Aromatic and Heterocyclic Building Blocks

2006

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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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“…[17] Trifluormethyllithium, [18] anders als beispielsweise Dibromfluormethyllithium, [19] zerfällt selbst bei tiefsten Temperaturen wegen unverzüglich einsetzender Eliminierungsund Substitutionsreaktionen. Andererseits kann Trifluormethanid (das Trifluormethyl-Anion) glatt aus (Trifluormethyl)trimethylsilan [20] oder Trifluormethan (Fluoroform) [21] freigesetzt und in situ abgefangen werden. Unter solchen Bedingungen lassen sich natürlich nur hochreaktive Elektrophile, im Wesentlichen Carbonyl-Verbindungen, umsetzen.…”

Section: Iod/trifluormethyl-austausch Unter Mitwirkung Von Kupferunclassified

CF₃‐substituierte aromatische und heterocyclische Bausteine

Schlosser

2006

Angewandte Chemie

188

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Fluor bleibt ein Geheimtipp in den Lebenswissenschaften, da sich mit diesem Element biologische Eigenschaften abstimmen lassen. Die Synthese fluorhaltiger Zielverbindungen ist jedoch nicht immer einfach: Praktisch jedes Fluor‐Atom, das an ein organisches Gerüst angeheftet wird, muss letztlich einer anorganischen Quelle entnommen werden. Ausschlaggebend für die Syntheseplanung ist die Entscheidung, auf welcher Stufe und wie das Halogen eingeführt werden soll. Gängige technische Verfahren, insbesondere die Verdrängung von Chlor mit wasserfreiem Fluorwasserstoff oder mit Kaliumfluorid, lassen sich schwerlich zweckmäßig im Labormaßstab ausführen. Allgemeingültige Methoden für Industrie wie Hochschulbereich finden deshalb großen Anklang. Für die Synthese CF3‐substituierter Arene oder Heterocyclen gibt es zwei hervorragende Möglichkeiten: Die CF3‐Gruppe kann paketweise durch Kupplung eines geeigneten Substrats mit in situ erzeugtem (Trifluormethyl)kupfer übertragen werden, oder man kann von einem CF3‐haltigen Aren oder Heterocyclus als Grundgerüst ausgehen und dieses mit den noch fehlenden Teilen vervollständigen.

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Fluoroform: an Efficient Precursor for the Trifluoromethylation of Aldehydes

Cited by 119 publications

References 57 publications

Application of fluoroform in trifluoromethylation and diﬂuoromethylation reactions

Application of fluoroform in trifluoromethylation and diﬂuoromethylation reactions

CF₃‐Bearing Aromatic and Heterocyclic Building Blocks

CF₃‐substituierte aromatische und heterocyclische Bausteine

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Fluoroform: an Efficient Precursor for the Trifluoromethylation of Aldehydes

Cited by 119 publications

References 57 publications

Application of fluoroform in trifluoromethylation and diﬂuoromethylation reactions

Application of fluoroform in trifluoromethylation and diﬂuoromethylation reactions

CF3‐Bearing Aromatic and Heterocyclic Building Blocks

CF3‐substituierte aromatische und heterocyclische Bausteine

Contact Info

Product

Resources

About

CF₃‐Bearing Aromatic and Heterocyclic Building Blocks

CF₃‐substituierte aromatische und heterocyclische Bausteine