Fluorinated acetylenic alcohols and derived allenes

Dear, R. E. A.; Gilbert, Everett E.

doi:10.1021/jo01266a070

Cited by 24 publications

(10 citation statements)

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“…The synthesis of propargylic fluorides can be accomplished by the deoxyfluorination of propargylic alcohols with DAST146 or fluorination of a variety of activated propargylic substrates147 such as propargylic mesylates or silyl ethers. Other commonly used deoxofluorinating reagents for the synthesis of propargylic fluorides include SF 4 ,147a,b, 148 dialkylaminosulfur trifluorides,147c,d,f,g Yarovenko’s reagent (Figure 2),149 and Ghosez’s reagent ( N , N ‐diisopropyl‐1‐fluoro‐2‐methylpropenamine) 150. Grée and co‐workers achieved the synthesis of chiral propargylic fluorides through an S N 2 reaction between chiral, nonracemic propargylic alcohols and fluoride 151.…”

Section: Fluorinationmentioning

confidence: 99%

Introduction of Fluorine and Fluorine‐Containing Functional Groups

Liang¹,

Neumann²,

Ritter³

2013

Angew Chem Int Ed

2,303

856

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Over the past decade, the most significant, conceptual advances in the field of fluorination were enabled most prominently by organo‐ and transition‐metal catalysis. The most challenging transformation remains the formation of the parent CF bond, primarily as a consequence of the high hydration energy of fluoride, strong metal—fluorine bonds, and highly polarized bonds to fluorine. Most fluorination reactions still lack generality, predictability, and cost‐efficiency. Despite all current limitations, modern fluorination methods have made fluorinated molecules more readily available than ever before and have begun to have an impact on research areas that do not require large amounts of material, such as drug discovery and positron emission tomography. This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field.

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Section: Fluorinationmentioning

confidence: 99%

Introduction of Fluorine and Fluorine‐Containing Functional Groups

Liang¹,

Neumann²,

Ritter³

2013

Angew Chem Int Ed

2,303

856

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“…1,1,1‐Trifluoro‐2‐(trifluoromethyl)‐3‐butyn‐2‐ol (4): Alkyne 4 was prepared by literature procedures, but with a modified workup method 12,22…”

Section: Methodsmentioning

confidence: 99%

“…Alkyne 4 was prepared by literature procedures, but with a modified workup method. [12,22] An oven-dried Carius tube was purged with nitrogen while cooling, charged with a stirring bar and ethynylmagnesium bromide (20 mL, 0.5 m in THF) was added. After this, gaseous hexafluoroacetone (1 equiv.)…”

Section: 11-trifluoro-2-(trifluoromethyl)-3-butyn-2-ol (4)mentioning

confidence: 99%

Biologically Active Trifluoromethyl‐Substituted Metallocene Triazoles: Characterization, Electrochemistry, Lipophilicity, and Cytotoxicity

2012

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We report the facile synthesis of four different trifluoromethylated metallocene triazoles and their biological evaluation (M = Fe and Ru). The cytotoxicity of all compounds was evaluated using MCF-7, HT-29, PT-45 and GM5657 cells and IC 50 values as low as 33 μM were found. It was shown that the metallocene moiety is crucial for the cytotoxic effect. The electrochemical behavior of triazoles 3-6 was investigated by [a]

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“…26, R = CF 3 ) gave only the fluorinated allene (not shown), likely by an intramolecular S N I process. 37 The propargylic fluorides 51 and 52, analogues of Danazol, a steroidal-type molecule, were obtained by the same method, albeit in low yields. During fluorination, the major compound was the product coming from a Wagner-Meerwein rearrangement.…”

Section: Synthesis Of Propargylic Derivatives With a Cfr 1 R 2 Substimentioning

confidence: 99%

Synthesis of Propargylic Fluorides toward Carbo- and Heterocycles with Mono- and gem-Difluorinated Side Chains

et al. 2017

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International audienceThis review reports the synthesis of propargylic derivatives with alkyl chains bearing either one fluorine or a gem-difluoro system. The preparation of the different categories of fluorinated derivatives is analyzed in a systematic manner, based on the nature of substituents close to the fluorine atom(s). In the second part of this review are summarized the synthetic applications of these fluorinated propargylic intermediates, focusing mainly on the preparation of carbo- and heterocyclic derivatives. 1 Introduction 2 Synthesis of Propargylic Fluorides 3 Use of Propargylic Fluorides in the Preparation of Carbo- and Heterocycles with Fluorine-Containing Side Chains 4 Conclusions and Perspectives © Georg Thieme VerlagStuttgart · New York

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Fluorinated acetylenic alcohols and derived allenes

Cited by 24 publications

References 0 publications

Introduction of Fluorine and Fluorine‐Containing Functional Groups

Introduction of Fluorine and Fluorine‐Containing Functional Groups

Biologically Active Trifluoromethyl‐Substituted Metallocene Triazoles: Characterization, Electrochemistry, Lipophilicity, and Cytotoxicity

Synthesis of Propargylic Fluorides toward Carbo- and Heterocycles with Mono- and gem-Difluorinated Side Chains

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