Trifluoromethyl Selenoxides: Electrophilic Reagents for C-H Trifluoromethylselenolation of (Hetero)Arene

被引：22

作者：

Li, Yang ^{[1
]}

Wang, Yanan ^{[1
]}

Ye, Zhegao ^{[1
]}

Zhang, Shangbiao ^{[1
]}

Ye, Xiaodong ^{[1
]}

Yuan, Zheliang ^{[1
]}

机构：

[1] Zhejiang Normal Univ, Dept Chem, Key Lab, Minist Educ Adv Catalysis Mat, Jinhua 321004, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 16期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/acs.orglett.2c00916

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trifluoromethylselenyl group (CF3Se) has become an emerging fluorinated moiety in synthetic chemistry due to its high Hansch lipophilicity parameter and strong electron-withdrawing effect. The trifluoromethylselenolation is hampered by limited synthetic methods and related reagents. Herein, we designed and synthesized the new electrophilic trifluoromethylselenolation reagents, trifluoromethyl selenoxides, which are easy to prepare and easy-to-handle and are not moisture or air sensitive. The selenoxides are successfully applied to metal-free C-H trifluoromethylselenolation of a series of (hetero)arenes.

引用

页码：3009 / 3013

页数：5

共 46 条

[1]

[Anonymous], 2008, CHEM SOC REV, V37, P330

[2] Highly Efficient C-SeCF3 Coupling of Aryl Iodides Enabled by an Air-Stable Dinuclear PdI Catalyst [J].

Aufiero, Marialuisa ;

Sperger, Theresa ;

Tsang, Althea S. -K. ;

Schoenebeck, Franziska .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (35) :10322-10326

[3]

Block E., CHEMBIOCHEM

[4]

Chang X.-H., ASIAN J ORG CHEM, V2021, P61

[5] Synthesis of CuI Trifluoromethylselenates for Trifluoromethylselenolation of Aryl and Alkyl Halides [J].

Chen, Chaohuang ;

Ouyang, Li ;

Lin, Quanfu ;

Liu, Yanpin ;

Hou, Chuanqi ;

Yuan, Yaofeng ;

Weng, Zhiqiang .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (03) :657-661

[6] ORGANOMETALLIC AND ORGANOMETALLOIDAL FLUORINE COMPOUNDS .14. TRIFLUOROMETHYL DERIVATIVES OF SELENIUM [J].

DALE, JW ;

EMELEUS, HJ ;

HASZELDINE, RN .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (SEP) :2939-2945

[7] Visible-Light-Induced Metal-Free Trifluoromethylselenolation of Electron-Rich Heteroarenes Using the Nucleophilic [Me4N][SeCF3] Reagent [J].

De Zordo-Banliat, Arnaud ;

Barthelemy, Lucas ;

Bourdreux, Flavien ;

Tuccio, Beatrice ;

Dagousset, Guillaume ;

Pegot, Bruce ;

Magnier, Emmanuel .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (04) :506-509

[8] Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents [J].

Dix, Stefan ;

Jakob, Michael ;

Hopkinson, Matthew N. .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (32) :7635-7639

[9]

Dong T., CHEMMEDCHEM, V2021, P3177

[10] Catalyst- and Additive-Free Trifluoromethylselenolation with [Me4N][SeCF3] [J].

Dong, Tao ;

He, Jian ;

Li, Zhi-Han ;

Zhang, Cheng-Pan .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (01) :1327-1335

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