Diphenyliodonium-Catalyzed Fluorination of Arynes: Synthesis of ortho-Fluoroiodoarenes

被引：54

作者：

Zeng, Yuwen ^{[1
]}

Li, Guangyu ^{[1
]}

Hu, Jinbo ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 37期

基金：

中国国家自然科学基金;

关键词：

arynes; fluorine; hypervalent compounds; Lewis acids; synthetic methods; COPPER-MEDIATED FLUORINATION; C-H FLUORINATION; DIARYLIODONIUM SALTS; POLYVALENT IODINE; ORGANIC-SYNTHESIS; AR-F; FLUORIDE; EXCHANGE; CHEMISTRY; BENZYNE;

D O I：

10.1002/anie.201503308

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Described is a one-pot vicinal fluorination-iodination of arynes at room temperature. The diphenyliodonium salt proved to be a privileged catalyst for this nucleophilic fluorination process using CsF as a fluorine source, and a subsequent facile electrophilic iodination with C4F9I was also found to be crucial to ensure the efficient fluorination. This new synthetic protocol has a broad substrate scope under mild reaction conditions.

引用

页码：10773 / 10777

页数：5

共 46 条

[21] An Efficient Route for the Synthesis of Isochromenocarbazolones through Palladium-Catalyzed Intramolecular ortho-Arylation
Sreenivas, Devanga K.
Nagarajan, Rajagopal
SYNTHESIS-STUTTGART, 2011, (19): : 3195 - 3203
[22] Synthesis of Isocoumarins through Three-Component Couplings of Arynes, Terminal Alkynes, and Carbon Dioxide Catalyzed by an NHC-Copper Complex
Yoo, Woo-Jin
Nguyen, Thanh V. Q.
Kobayashi, Shu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10213 - 10217
[23] Pd(PPh3)4-catalyzed direct ortho-fluorination of 2-arylbenzothiazoles with an electrophilic fluoride N-fluorobenzenesulfonimide (NFSI)
Ding, Qiuping
Ye, Changqing
Pu, Shouzhi
Cao, Banpeng
TETRAHEDRON, 2014, 70 (02) : 409 - 416
[24] Arylnaphthalene lignans through Pd-catalyzed [2+2+2] cocyclization of arynes and diynes: Total synthesis of taiwanins C and E
Sato, Y
Tamura, T
Mori, M
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) : 2436 - 2440
[25] Cascade Nucleophilic Addition-Cyclic Michael Addition of Arynes and Phenols/Anilines Bearing Ortho α,β-Unsaturated Groups: Facile Synthesis of 9-Functionalized Xanthenes/Acridines
Huang, Xian
Zhang, Tiexin
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (02) : 506 - 509
[26] N-Heterocyclic Carbene Catalyzed Enantioselective α-Fluorination of Aliphatic Aldehydes and α-Chloro Aldehydes: Synthesis of α-Fluoro Esters, Amides, and Thioesters
Dong, Xiuqin
Yang, Wen
Hu, Weimin
Sun, Jianwei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) : 660 - 663
[27] Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed Ortho-Olefination and Decarboxylation of Benzoic Acids
Mochida, Satoshi
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
ORGANIC LETTERS, 2010, 12 (24) : 5776 - 5779
[28] Palladium-catalyzed cleavage of the Me-Si bond in ortho-trimethylsilyl aryltriflates: synthesis of benzosilole derivatives from ortho-trimethylsilyl aryltriflates and alkynes
Meng, Tianhao
Ouyang, Kunbing
Xi, Zhenfeng
RSC ADVANCES, 2013, 3 (34): : 14273 - 14276
[29] Nickel-catalyzed [4+2] Cycloaddition of Styrenes with Arynes via 1:1 Cross-coupling: Synthesis of 9,10-Dihydrophenanthrenes
Kubo, Teruhiko
Fujita, Takeshi
Ichikawa, Junji
CHEMISTRY LETTERS, 2020, 49 (03) : 264 - 266
[30] Palladium-catalyzed reaction of arynes with a bis-π-allyl palladium complex.: An efficient method for the synthesis of 1,2-diallylated derivatives of benzene
Yoshikawa, E
Radhakrishnan, KV
Yamamoto, Y
TETRAHEDRON LETTERS, 2000, 41 (05) : 729 - 731

← 1 2 3 4 5 →