Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles

被引：45

作者：

Wen, Si ^{[1
]}

Tian, Qingyu ^{[1
]}

Chen, Yanhui ^{[1
]}

Zhang, Yuqing ^{[1
]}

Cheng, Guolin ^{[1
]}

机构：

[1] Huaqiao Univ, Coll Mat Sci & Engn, Instrumental Anal Ctr, Xiamen Key Lab Optoelect Mat & Adv Mfg, Xiamen 361021, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 19期

关键词：

C-H BONDS; SELECTIVE SYNTHESIS; PYRROLES; DERIVATIVES; ACTIVATION; FLUORINE; TRIFLUOROMETHYLATION; GENERATION; INSERTION; ALKENES;

D O I：

10.1021/acs.orglett.1c02598

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, and the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have been obtained in 27-78% yield. This reaction features a broad substrate scope and generates dimethyl sulfoxide and H2O as byproducts.

引用

收藏

页码：7407 / 7411

页数：5

相关论文

共 55 条

[1] A novel melatonin derivative modulates sleep-wake cycle in rats [J].

Akanmu, MA ;

Songkram, C ;

Kagechika, H ;

Honda, K .

NEUROSCIENCE LETTERS, 2004, 364 (03) :199-202

[2] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds [J].

Barday, Manuel ;

Janot, Christopher ;

Halcovitch, Nathan R. ;

Muir, James ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13117-13121

[3] Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale [J].

Beatty, Joel W. ;

Douglas, James J. ;

Miller, Richard ;

McAtee, Rory C. ;

Cole, Kevin P. ;

Stephenson, Corey R. J. .

CHEM, 2016, 1 (03) :456-472

[4] Rh(iii)-Catalyzed C-H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones [J].

Cai, Libo ;

Zhu, Xiaoyi ;

Chen, Jiayi ;

Lin, Aijun ;

Yao, Hequan .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21) :3688-3692

[5] α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles [J].

Caiuby, Clarice A. D. ;

de Jesus, Matheus P. ;

Burtoloso, Antonio C. B. .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11) :7433-7445

[6] Computational Studies on Reaction Mechanism of the Catalyst-Controlled Selective Insertion of Metal Carbenoids into C-C and C-H Bonds of 1,3-Dicarbonyl Compounds [J].

Cao, Shanshan ;

Liu, Zhaohong ;

Yuan, Haiyan ;

Yang, Liu ;

Zhang, Jingping ;

Bi, Xihe .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (08) :2468-2475

[7] External Reductant-Free Palladium-Catalyzed Reductive Insertion of Isocyanide: Synthesis of Polysubstituted Pyrroles and Its Applications as a Cysteine Probe [J].

Chen, Dianpeng ;

Shan, Yingying ;

Li, Jianming ;

You, Jinmao ;

Sun, Xuejun ;

Qiu, Guanyinsheng .

ORGANIC LETTERS, 2019, 21 (11) :4044-4048

[8] Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4-a]indolone and Dihydropyrimido [1,6-a]indolone via Rh(III)-catalyzed [3+3] or [4+2] C-H Annulation [J].

Chen, Junyu ;

Zhong, Tianshuo ;

Zheng, Xiangyun ;

Yin, Chuanliu ;

Zhang, Lei ;

Zhou, Jian ;

Jiang, Xinpeng ;

Yu, Chuanming .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) :446-452

[9] Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls [J].

Clare, Daniel ;

Dobson, Benjamin C. ;

Inglesby, Phillip A. ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (45) :16198-16202

[10] Recent advances in the synthesis of pyrroles by multicomponent reactions [J].

Estevez, Veronica ;

Villacampa, Mercedes ;

Menendez, J. Carlos .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4633-4657

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