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Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles via condensation of diamines or amino(thio)phenols with CF3CN SCIE
期刊论文 | 2023 , 21 (23) , 4788-4793 | ORGANIC & BIOMOLECULAR CHEMISTRY
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Abstract :

A new and efficient method is developed for the synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles in good to excellent yields by the condensation of diamines or amino(thio)phenols with in situ generated CF3CN. Additionally, the synthetic utility of the 2-trifluoromethyl benzimidazole and benzoxazole products is demonstrated via gram scale synthesis. The mechanistic study suggests that the reaction proceeds via the nucleophilic addition of trifluoroacetonitrile to the amino group of the diamine derivatives to form an imidamide intermediate, followed by intramolecular cyclization.

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GB/T 7714 Lin, Bo , Yao, Yunfei , Wu, Minze et al. Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles via condensation of diamines or amino(thio)phenols with CF3CN [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2023 , 21 (23) : 4788-4793 .
MLA Lin, Bo et al. "Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles via condensation of diamines or amino(thio)phenols with CF3CN" . | ORGANIC & BIOMOLECULAR CHEMISTRY 21 . 23 (2023) : 4788-4793 .
APA Lin, Bo , Yao, Yunfei , Wu, Minze , Qin, Lu , Chen, Shouxiong , You, Yi et al. Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles via condensation of diamines or amino(thio)phenols with CF3CN . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2023 , 21 (23) , 4788-4793 .
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Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles via condensation of diamines or amino(thio)phenols with CF3CN EI
期刊论文 | 2023 , 21 (23) , 4788-4793 | Organic and Biomolecular Chemistry
Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles via condensation of diamines or amino(thio)phenols with CF3CN Scopus
期刊论文 | 2023 , 21 (23) , 4788-4793 | Organic and Biomolecular Chemistry
Copper-mediated three-component synthesis of 2-trifluoromethyl benzimidazoles SCIE
期刊论文 | 2022 , 9 (12) , 3247-3254 | ORGANIC CHEMISTRY FRONTIERS
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Abstract :

A copper-mediated three-component reaction of o-iodoanilines, anilines, and ethyl trifluoropyruvate is reported. The transformation allows diverse substrate scope on both o-iodoanilines and anilines, delivering various 2-trifluoromethylbenzimidazole products in moderate to good yields. Mechanistic studies suggest that this transformation proceeds via condensation of o-iodoaniline with ethyl trifluoropyruvate, followed by an intermolecular Ullmann-type cross-coupling reaction with aniline and intramolecular amination.

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GB/T 7714 You, Chenhui , Huang, Yangjie , You, Yi et al. Copper-mediated three-component synthesis of 2-trifluoromethyl benzimidazoles [J]. | ORGANIC CHEMISTRY FRONTIERS , 2022 , 9 (12) : 3247-3254 .
MLA You, Chenhui et al. "Copper-mediated three-component synthesis of 2-trifluoromethyl benzimidazoles" . | ORGANIC CHEMISTRY FRONTIERS 9 . 12 (2022) : 3247-3254 .
APA You, Chenhui , Huang, Yangjie , You, Yi , Weng, Zhiqiang . Copper-mediated three-component synthesis of 2-trifluoromethyl benzimidazoles . | ORGANIC CHEMISTRY FRONTIERS , 2022 , 9 (12) , 3247-3254 .
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Copper-mediated three-component synthesis of 2-trifluoromethyl benzimidazoles EI
期刊论文 | 2022 , 9 (12) , 3247-3254 | Organic Chemistry Frontiers
Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3+2]-Cycloaddition of Nitrile Imines with CF3CN SCIE
期刊论文 | 2022 , 27 (19) | MOLECULES
WoS CC Cited Count: 6
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Abstract :

We herein describe a general approach to 5-trifluoromethyl 1,2,4-triazoles via the [3 + 2]-cycloaddition of nitrile imines generated in situ from hydrazonyl chloride with CF3CN, utilizing 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as the precursor of trifluoroacetonitrile. Various functional groups, including alkyl-substituted hydrazonyl chloride, were tolerated during cycloaddition. Furthermore, the gram-scale synthesis and common downstream transformations proved the potential synthetic relevance of this developed methodology.

Keyword :

cycloaddition cycloaddition nitrile imines nitrile imines triazole triazole trifluoroacetonitrile trifluoroacetonitrile trifluoromethyl trifluoromethyl

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GB/T 7714 Lin, Bo , Zhang, Zipeng , Yao, Yunfei et al. Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3+2]-Cycloaddition of Nitrile Imines with CF3CN [J]. | MOLECULES , 2022 , 27 (19) .
MLA Lin, Bo et al. "Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3+2]-Cycloaddition of Nitrile Imines with CF3CN" . | MOLECULES 27 . 19 (2022) .
APA Lin, Bo , Zhang, Zipeng , Yao, Yunfei , You, Yi , Weng, Zhiqiang . Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3+2]-Cycloaddition of Nitrile Imines with CF3CN . | MOLECULES , 2022 , 27 (19) .
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Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF3CN Scopus
期刊论文 | 2022 , 27 (19) | Molecules
Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester SCIE
期刊论文 | 2022 , 20 (17) , 3564-3569 | ORGANIC & BIOMOLECULAR CHEMISTRY
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Abstract :

A base promoted annulation of pyridinium ylides with trifluoroacetyl diazoester has been reported. Highly functionalized 4-trifluoromethyl pyridazines were synthesized in good yields without the use of any heavy metal catalysts. The developed methodology was compatible with a variety of important functional groups. Mechanistic studies revealed that trifluoroacetylated hydrazone was an active intermediate of this three-component annulation. Synthetic versatility of the method via aminolysis and condensation toward amide- and pyridazino[4,5-c]pyridazine-derivatives has been showcased.

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GB/T 7714 Fang, Zheng , Teng, Yun , Yang, Huilin et al. Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2022 , 20 (17) : 3564-3569 .
MLA Fang, Zheng et al. "Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester" . | ORGANIC & BIOMOLECULAR CHEMISTRY 20 . 17 (2022) : 3564-3569 .
APA Fang, Zheng , Teng, Yun , Yang, Huilin , Li, Rongxing , Li, Qiuhong , You, Yi et al. Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2022 , 20 (17) , 3564-3569 .
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Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester EI
期刊论文 | 2022 , 20 (17) , 3564-3569 | Organic and Biomolecular Chemistry
Recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides SCIE CSCD
期刊论文 | 2022 , 33 (10) , 4517-4530 | CHINESE CHEMICAL LETTERS
WoS CC Cited Count: 17
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Abstract :

Fluoroalkyl-containing organic compounds have exhibited wide applications in the field of pharmaceuticals, agrochemicals and materials science due to their outstanding properties such as biological activity, metabolic stability, lipophilicity, excellent chemical and thermal stability. Therefore, various synthetic strategies have been developed for the construction of fluoroalkyl-containing compounds, using highly active fluorinating reagents and fluorinated building blocks. Recently, the use of easily available and inexpensive trifluoroacetic anhydride (TFAA) and its anhydride analogues has attracted great attention to access numerous fluoroalkyl-containing compounds through cyclization and coupling reactions. In this review, we summarized the recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides as reagents. This review aims to provide a reference for researchers on how to develop new synthetic straregies of fluorine-containing organic compounds and achieve kilograms or even tons preparation of fluorine-containing organic compounds using fluoroalkyl anhydrides. (C) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Keyword :

Coupling reaction Coupling reaction Cyclization reaction Cyclization reaction Fluoroalkanoyl Fluoroalkanoyl Fluoroalkl Fluoroalkl Fluoroalkyl anhydride Fluoroalkyl anhydride Fluoroalkyl-containing organic compound Fluoroalkyl-containing organic compound Trifluoroacetic anhydride (TFAA) Trifluoroacetic anhydride (TFAA)

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GB/T 7714 Wu, Wei , You, Yi , Weng, Zhiqiang . Recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides [J]. | CHINESE CHEMICAL LETTERS , 2022 , 33 (10) : 4517-4530 .
MLA Wu, Wei et al. "Recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides" . | CHINESE CHEMICAL LETTERS 33 . 10 (2022) : 4517-4530 .
APA Wu, Wei , You, Yi , Weng, Zhiqiang . Recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides . | CHINESE CHEMICAL LETTERS , 2022 , 33 (10) , 4517-4530 .
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Recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides Scopus CSCD
期刊论文 | 2022 , 33 (10) , 4517-4530 | Chinese Chemical Letters
An aerobic copper-mediated domino process for the synthesis of 3-(trifluoromethylseleno)indoles SCIE
期刊论文 | 2022 , 20 (10) , 2115-2120 | ORGANIC & BIOMOLECULAR CHEMISTRY
WoS CC Cited Count: 4
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Abstract :

An aerobic copper-mediated domino reaction for the synthesis of 3-(trifluoromethylseleno)indoles by trifluoromethylselenolation of N-Ts 2-alkynylaniline with [(bpy)CuSeCF3](2) is reported. This reaction proceeds through sequential oxidation, alkyne coordination, and deprotonation followed by reductive elimination. This mild and robust method is highly functional group tolerant and provides straightforward access to 3-(trifluoromethylseleno)indoles in moderate to good yields.

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GB/T 7714 Wang, Hui , Yao, Yunfei , You, Yi et al. An aerobic copper-mediated domino process for the synthesis of 3-(trifluoromethylseleno)indoles [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2022 , 20 (10) : 2115-2120 .
MLA Wang, Hui et al. "An aerobic copper-mediated domino process for the synthesis of 3-(trifluoromethylseleno)indoles" . | ORGANIC & BIOMOLECULAR CHEMISTRY 20 . 10 (2022) : 2115-2120 .
APA Wang, Hui , Yao, Yunfei , You, Yi , Huang, Yangjie , Weng, Zhiqiang . An aerobic copper-mediated domino process for the synthesis of 3-(trifluoromethylseleno)indoles . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2022 , 20 (10) , 2115-2120 .
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An aerobic copper-mediated domino process for the synthesis of 3-(trifluoromethylseleno)indoles EI
期刊论文 | 2022 , 20 (10) , 2115-2120 | Organic and Biomolecular Chemistry
Ring-expansion reaction for the synthesis of 2-(trifluoromethyl)oxazoles and 3-(trifluoromethyl)-1,2,4-triazines SCIE
期刊论文 | 2022 , 107 | TETRAHEDRON LETTERS
WoS CC Cited Count: 6
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Abstract :

A ring-expansion reaction of 2H-azirine with trifluoroacetic anhydride for the synthesis of 2-(trifluo-romethyl)oxazoles is disclosed. The reaction features readily available reactants, relatively mild condi-tions, and high yields of products. The generated 2-(trifluoromethyl)oxazole core could be easily converted into 3-(trifluoromethyl)-1,2,4-triazines through hydrazinolysis reaction.(c) 2022 Elsevier Ltd. All rights reserved.

Keyword :

1 1 2 2 4-Triazine 4-Triazine Oxazole Oxazole Ring-expansion reaction Ring-expansion reaction Trifluoroacetic anhydride Trifluoroacetic anhydride Trifluoromethyl Trifluoromethyl

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GB/T 7714 Teng, Yun , Fang, Tingyu , Lin, Zitong et al. Ring-expansion reaction for the synthesis of 2-(trifluoromethyl)oxazoles and 3-(trifluoromethyl)-1,2,4-triazines [J]. | TETRAHEDRON LETTERS , 2022 , 107 .
MLA Teng, Yun et al. "Ring-expansion reaction for the synthesis of 2-(trifluoromethyl)oxazoles and 3-(trifluoromethyl)-1,2,4-triazines" . | TETRAHEDRON LETTERS 107 (2022) .
APA Teng, Yun , Fang, Tingyu , Lin, Zitong , Qin, Lu , Jiang, Mengfan , Wu, Wei et al. Ring-expansion reaction for the synthesis of 2-(trifluoromethyl)oxazoles and 3-(trifluoromethyl)-1,2,4-triazines . | TETRAHEDRON LETTERS , 2022 , 107 .
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Ring-expansion reaction for the synthesis of 2-(trifluoromethyl)oxazoles and 3-(trifluoromethyl)-1,2,4-triazines Scopus
期刊论文 | 2022 , 107 | Tetrahedron Letters
从化学实验竞赛探讨高校化学实验教学的改革和创新——第11届全国大学生化学实验邀请赛理论试题的解析与思考 PKU
期刊论文 | 2021 , 42 (6) , 61-64 | 化学教育
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Abstract :

从命题思路、试题内容及特点和结果分析等3个方面对第11届全国大学生化学实验邀请赛的理论试题进行讨论分析和总结,同时对化学实验教学的改革提出几点思考和建议,以期促进高校化学实验教学的改革和创新.

Keyword :

化学实验邀请赛 化学实验邀请赛 实验教学改革 实验教学改革 实验理论试题 实验理论试题

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GB/T 7714 郑琤 , 魏巧华 , 汤儆 et al. 从化学实验竞赛探讨高校化学实验教学的改革和创新——第11届全国大学生化学实验邀请赛理论试题的解析与思考 [J]. | 化学教育 , 2021 , 42 (6) : 61-64 .
MLA 郑琤 et al. "从化学实验竞赛探讨高校化学实验教学的改革和创新——第11届全国大学生化学实验邀请赛理论试题的解析与思考" . | 化学教育 42 . 6 (2021) : 61-64 .
APA 郑琤 , 魏巧华 , 汤儆 , 游毅 . 从化学实验竞赛探讨高校化学实验教学的改革和创新——第11届全国大学生化学实验邀请赛理论试题的解析与思考 . | 化学教育 , 2021 , 42 (6) , 61-64 .
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Copper-catalyzed one-pot synthesis of 2-(2,2,2-trifluoroethyl)-substituted benzofused heterocycles SCIE
期刊论文 | 2021 , 8 (9) , 1997-2001 | ORGANIC CHEMISTRY FRONTIERS
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A novel synthesis approach for the construction of 2-trifluoroethyl-substituted benzofurans under copper-catalyzed conditions has been developed. The reaction of salicylaldehyde p-tosylhydrazones with 2-bromo-3,3,3-trifluoropropene proceeded through a sequential process to afford products in moderate to excellent yields (up to 93%). This method is also applicable to the formation of 2-trifluoroethylated indoles.

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GB/T 7714 Wu, Wei , Luo, Beibei , You, Yi et al. Copper-catalyzed one-pot synthesis of 2-(2,2,2-trifluoroethyl)-substituted benzofused heterocycles [J]. | ORGANIC CHEMISTRY FRONTIERS , 2021 , 8 (9) : 1997-2001 .
MLA Wu, Wei et al. "Copper-catalyzed one-pot synthesis of 2-(2,2,2-trifluoroethyl)-substituted benzofused heterocycles" . | ORGANIC CHEMISTRY FRONTIERS 8 . 9 (2021) : 1997-2001 .
APA Wu, Wei , Luo, Beibei , You, Yi , Weng, Zhiqiang . Copper-catalyzed one-pot synthesis of 2-(2,2,2-trifluoroethyl)-substituted benzofused heterocycles . | ORGANIC CHEMISTRY FRONTIERS , 2021 , 8 (9) , 1997-2001 .
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Copper-catalyzed one-pot synthesis of 2-(2,2,2-trifluoroethyl)-substituted benzofused heterocycles EI
期刊论文 | 2021 , 8 (9) , 1997-2001 | Organic Chemistry Frontiers
A method for synthesis of polysubstituted 4-difluoromethyl and perfluoroalkyl pyrazoles SCIE
期刊论文 | 2021 , 85 | TETRAHEDRON
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Abstract :

A method for the synthesis of polysubstituted 4-difluoromethyl and perfluoroalkyl pyrazole derivatives by the Lewis acid- and base-co-mediated reaction of perfluoroacetyl diazoester with ketones is reported. A series of structurally diverse 4-difluoromethylated and perfluoroalkylated pyrazoles were obtained in moderate to good yields. The reactions proceeded smoothly under mild conditions with wide functional group tolerance. (C) 2021 Elsevier Ltd. All rights reserved.

Keyword :

Difluoromethyl Difluoromethyl Fluorine Fluorine Perfluoroalkyl Perfluoroalkyl Pyrazole Pyrazole

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GB/T 7714 Chen, Huahong , Wen, Shunli , Cui, Yubo et al. A method for synthesis of polysubstituted 4-difluoromethyl and perfluoroalkyl pyrazoles [J]. | TETRAHEDRON , 2021 , 85 .
MLA Chen, Huahong et al. "A method for synthesis of polysubstituted 4-difluoromethyl and perfluoroalkyl pyrazoles" . | TETRAHEDRON 85 (2021) .
APA Chen, Huahong , Wen, Shunli , Cui, Yubo , Lin, Lu , Zhang, Hanbang , Fang, Zheng et al. A method for synthesis of polysubstituted 4-difluoromethyl and perfluoroalkyl pyrazoles . | TETRAHEDRON , 2021 , 85 .
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