Recent Progress Toward the Synthesis of Trifluoromethyl‐ and Difluoromethyl‐Substituted Cyclopropanes

Bos, Maxence; Poisson, Thomas; Pannecoucke, Xavier; Charette, André B.; Jubault, Philippe

doi:10.1002/chem.201604564

Cited by 110 publications

(50 citation statements)

References 75 publications

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“…2018 年, 该课题组 [41] 又利用手性 [42] . 在众多合成方法中, 由于氟代硫叶立德具有易得、稳定和易操作等优点, 基于其与活化烯烃的 Johnson-Corey-Chaykovsky 反应引起了人们的关注 [43] . 2019 年, 黄伟课题组 [44] 将橙酮氮杂二烯用作特殊缺电子双键反应底物, 通过它与氟化硫叶立德的形式[2＋1]环化反应, 合成了一系列具有三氟甲基取代的苯并呋喃螺环丙烷骨架, 进一步拓展了橙酮氮杂二烯的反应性, 并为具有类似核心骨架的天然产物和生物活性分子提供了新合成方法(Scheme 20a); 多米诺反应作为合成具有复杂结构分子的有效方法已得到有机合成化学家的广泛关注.…”

Section: 环化反应unclassified

Recent Progress in the Reactions of Aurone-Derived Azadienes

Yu¹,

Gao²,

Lan³

et al. 2020

Chin. J. Org. Chem.

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Owing to the important physiological and pharmacological activities of benzofuran compounds, the exploration for efficient synthesis methods is of great value and wide application. Aurone-derived azadienes have been identified to be effective reactants in the field of organic synthesis owing to the driving force of aromatization. A large number of reactions based on 1,4-conjugate addition and tandem cyclization have been reported, which exhibited great advantages in the construction of heterocycles with benzofuran skeletons. In this paper, the recent progress in the chemical transformations of aurone-derived azadienens is reviewed, with emphasis on the employed catalytic system and the plausible mechanism of some reactions.

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Section: 环化反应unclassified

Recent Progress in the Reactions of Aurone-Derived Azadienes

Yu¹,

Gao²,

Lan³

et al. 2020

Chin. J. Org. Chem.

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“…Fluorinated cyclopropanes have become extraordinary structural motifs which attracted much attention in organic synthesis, drug discovery and agrochemistry over the last years . In particular, highly potent compounds bearing a gem ‐difluorocyclopropyl substituent were disclosed in recent patents, e.g.…”

Section: Introductionmentioning

confidence: 99%

N‐Difluorocyclopropyl‐Substituted Pyrazoles: Synthesis and Reactivity

et al. 2019

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Difluorocyclopropanation of N‐vinylazoles with the CF3SiMe3–NaI system was studied. It was found that N‐vinylpyrazoles could be transformed into the corresponding N‐difluorocyclopropyl‐substituted derivatives. The method was efficient on a 100 g scale and could be applied for the preparation of various functionalized regioisomeric pyrazole derivatives bearing a gem‐difluorocyclopropane moiety, such as amines, carboxylic acids, aldehydes, bromides, and boronic esters. It was found that N‐difluorocyclopropylpyrazole moiety tolerated many common reagents including nitrating mixture, bromine, aqueous acids and alkali, KMnO4, LiBH4, and Pd0 complexes; it was unstable towards AlCl3, catalytic hydrogenation and lithiation conditions. The products obtained are advanced building blocks which of potential importance to medicinal and agrochemistry.

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“…[13][14][15] In particular, significant advances have been achieved during the last decade in the development of new reagents and general approaches for trifluoromethylation, including electrophilic, radical and nucleophilic reactions. [16][17][18][19][20][21][22][23][24] Among these methods, the use of CF 3 H for installing directly the trifluoromethyl moiety into an organic compound remains an appealing approach, in terms of raw material availability and atom-economy. Nevertheless, as a greenhouse gas, CF 3 H must not be dispersed into the atmosphere.…”

Section: Introductionmentioning

confidence: 99%

Real-Time Spectroscopic Analysis Enabling Quantitative and Safe Consumption of Fluoroform during Nucleophilic Trifluoromethylation in Flow

Musio

Gala

Ley

2017

ACS Sustainable Chem. Eng.

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The productive use of toxic waste materials derived from industrial processes is one of the main goals of modern chemical research to increase sustainability of the large scale production. Here we devise a simple and robust strategy for the utilization of trifluoromethane, obtained in large quantities from polytetrafluoroethylene (PTFE) manufacture, and the conversion of this greenhouse gas into valuable fluorinated compounds. The generation of the trifluoromethyl carbanion and its direct and complete consumption through trapping with a number of electrophiles were achieved by a fully contained flow reactor setup. The adoption of modern in-line analytical tools, such as portable FT-IR and NMR devices, allowed the accurate reagent dosing with considerable benefits in terms of controlling the environmental impact during this continuous process. The advantages of the method, with respect to the batch procedure, will be discussed and demonstrated experimentally. 2

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Recent Progress Toward the Synthesis of Trifluoromethyl‐ and Difluoromethyl‐Substituted Cyclopropanes

Abstract: This Minireview describes recent advances toward the synthesis of trifluoromethyl- and difluoromethyl-substituted cyclopropanes. Synthetic methodologies using [2+1] cycloaddition, ring-contraction, and ring-closure cyclopropanations since 2010 are reported.

Cited by 110 publications

References 75 publications

Recent Progress in the Reactions of Aurone-Derived Azadienes

Recent Progress in the Reactions of Aurone-Derived Azadienes

N‐Difluorocyclopropyl‐Substituted Pyrazoles: Synthesis and Reactivity

Real-Time Spectroscopic Analysis Enabling Quantitative and Safe Consumption of Fluoroform during Nucleophilic Trifluoromethylation in Flow

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