Mechanistic aspects of acid-catalyzed reactions of 2,2,2-trifluorodiazoethane with alcohols

Loehr, D. T.; Armistead, David M.; Roy, J.; Dorn, Harry C.

doi:10.1016/s0022-1139(00)82783-9

Cited by 10 publications

(4 citation statements)

References 14 publications

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“…The reaction proceeded at room temperature and worked for aromatic (66), heteroaromatic (67), and aliphatic (68) substrates. Mechanistically, difluorocyclopropene 69 and CF 3 CHN 2 (1) first underwent [3 + 2]-cycloaddition into intermediate 70 (Scheme 14).…”

Section: Preparationmentioning

confidence: 99%

“…Six years later, the authors studied the reaction mechanism. 68 First, a protonation of CF 3 CHN 2 with HBF 4 took place to form the intermediate diazonium salt 197. The later reacted with nucleophiles in a bimolecular fashion to give nitrogen and the target products.…”

Section: Reaction With H + (Protonation)mentioning

confidence: 99%

“…All reactions were carried out in NMR tubes at room temperature. Six years later, the authors studied the reaction mechanism . First, a protonation of CF 3 CHN 2 with HBF 4 took place to form the intermediate diazonium salt 197 .…”

Section: Reactions As C-nucleophilementioning

confidence: 99%

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2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

Mykhailiuk

2020

Chem. Rev.

152

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2,2,2-Trifluorodiazoethane (CF3CHN2) has been proven to be a valuable reagent for the rapid synthesis of various classes of trifluoromethyl-substituted organic molecules in both academic and industrial research. The reagent was prepared first in 1943, but only recently it received a great attention from the scientific community. Protocols for in situ generation, in flow generation, and crystalline analogues of CF3CHN2 were developed during the past decade and have led to an ever-increasing number of publications on the topic. The current review summarizes and comprehensively analyzes all manuscripts in a peer-reviewed literature on 2,2,2-trifluorodiazoethane since its discovery in 1943 until today (as of 19 June 2020). These include contributions mostly overseen by scientific community before. A particular emphasis of this review is to classify the existing reactivity modes of CF3CHN2 and to systematically analyze the corresponding reaction mechanisms in details. At the end of this review, several undeveloped areas for CF3CHN2 are outlined, based on the overseen precedents in the literature.

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Section: Preparationmentioning

confidence: 99%

Section: Reaction With H + (Protonation)mentioning

confidence: 99%

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2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

Mykhailiuk

2020

Chem. Rev.

152

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“…16 This very unique transformation was applied to the preparation of sulpho protected glycosaminoglycans (15) by Linhardt and co-workers (Scheme 2). 17 In further investigations, the reaction of trifluorodiazoethane with alcohols, 18 glyoxylate, 19 chloral 20 and aldehydes 21 was studied. Additionally, trifluorodiazoethane was applied in the synthesis of pyrazoles 22 and in ring expansion reactions to yield 7-membered rings.…”

Section: Early Applicationsmentioning

confidence: 99%

Fluorinated diazoalkanes – a versatile class of reagents for the synthesis of fluorinated compounds

2016

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Although diazoalkanes find regular application in organic synthesis, the synthesis and application of their fluorinated homologues was long neglected. First described in 1943, trifluorodiazoethane found its way into the organic synthesis repertoire only in the past decade for atom-economical and practical synthesis of fluorinated building blocks and currently emerges as a versatile reagent. The synthetic applicability of this reagent is currently being investigated in great detail and many interesting new reactivities, and procedures for the synthesis of fluoroalkyl-substituted building blocks have been developed. In this context, a range of new fluoroalkyl substituted diazoalkanes have been introduced in the past few years, ranging from perfluorinated diazoalkanes towards highly reactive difluorodiazoethane which was first described in 2015. This tutorial review covers historic milestones of fluoroalkyl substituted diazoalkanes and highlights recent examples which underscore their vast potential to the synthesis of fluorinated compounds.

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Synthesis of CF₃CH₂‐Amides/Propiolamides/Acrylamides: The TfOH Catalyzed Reactions of Nitrile Compounds with CF₃CHN₂

Devi,

Kumar,

Lamba

et al. 2024

Adv Synth Catal

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An efficient and operationally simple protocol to access N‐(2,2,2‐trifluoroethyl)amides/propiolamides and acrylamides via direct conversion of easily accessible nitriles (aryl/alkyl/alkynyl/vinyl) and in situ generated CF3CHN2 as trifluoroethylating reagent has been developed. The protocol offers broad functional group tolerance under mild reaction conditions. Furthermore, the conversion of trifluoroethylated propiolamide into its triazole analog via Ru‐catalyzed [3+2] cycloadditions using BnN3 clearly indicates its versatility in the synthetic applications.

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Mechanistic aspects of acid-catalyzed reactions of 2,2,2-trifluorodiazoethane with alcohols

Cited by 10 publications

References 14 publications

2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

Fluorinated diazoalkanes – a versatile class of reagents for the synthesis of fluorinated compounds

Synthesis of CF₃CH₂‐Amides/Propiolamides/Acrylamides: The TfOH Catalyzed Reactions of Nitrile Compounds with CF₃CHN₂

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Mechanistic aspects of acid-catalyzed reactions of 2,2,2-trifluorodiazoethane with alcohols

Cited by 10 publications

References 14 publications

2,2,2-Trifluorodiazoethane (CF3CHN2): A Long Journey since 1943

2,2,2-Trifluorodiazoethane (CF3CHN2): A Long Journey since 1943

Fluorinated diazoalkanes – a versatile class of reagents for the synthesis of fluorinated compounds

Synthesis of CF3CH2‐Amides/Propiolamides/Acrylamides: The TfOH Catalyzed Reactions of Nitrile Compounds with CF3CHN2

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Product

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2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

Synthesis of CF₃CH₂‐Amides/Propiolamides/Acrylamides: The TfOH Catalyzed Reactions of Nitrile Compounds with CF₃CHN₂