9-Borabicyclo[3.3.l]nonane-induced Friedel-Crafts benzylation of arenes with benzyl fluorides

被引：15

作者：

Guo, Jing ^{[1
]}

Bamford, Karlee L. ^{[1
]}

Stephan, Douglas W. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 21期

基金：

加拿大自然科学与工程研究理事会;

关键词：

C-F ACTIVATION; BOND ACTIVATION; HYDRODEFLUORINATION; CENTERS;

D O I：

10.1039/c9ob00912d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Friedel-Crafts benzylation of arenes with benzyl fluorides using 9-borabicyclo[3.3.l]nonane (9-BBN) as a mediator has been developed. This provides a simple and cheap route to the activation of C-F bonds to synthesize 1,1-diarylmethanes in good to excellent yields (up to 98%) under mild conditions. Functional group tolerance and the mechanism are considered.

引用

页码：5258 / 5261

页数：4

共 4 条

[1] Synthesis of diarylmethanes via a Friedel-Crafts benzylation using arenes and benzyl alcohols in the presence of triphenylphosphine ditriflate
Khodaei, Mohammad Mehdi
Nazari, Ehsan
TETRAHEDRON LETTERS, 2012, 53 (38) : 5131 - 5135
[2] Heteropolyanion-based ionic liquid-functionalized mesoporous copolymer catalyst for Friedel-Crafts benzylation of arenes with benzyl alcohol
Li, Jing
Zhou, Yu
Mao, Dan
Chen, Guojian
Wang, Xiaochen
Yang, Xiaoning
Wang, Meng
Peng, Luming
Wang, Jun
CHEMICAL ENGINEERING JOURNAL, 2014, 254 : 54 - 62
[3] Benzylation of arenes through FeCl3-catalyzed Friedel-Crafts reaction via C-O activation of benzyl ether
Wang, Bi-Qin
Xiang, Shi-Kai
Sun, Zuo-Peng
Guan, Bing-Tao
Hu, Ping
Zhao, Ke-Qing
Shi, Zhang-Jie
TETRAHEDRON LETTERS, 2008, 49 (27) : 4310 - 4312
[4] Enantioselective synthesis of bicyclo[6.1.0]nonane-9-carboxylic acids via Me2AlOTf-promoted intramolecular friedel-crafts alkylation of arenes with the γ-lactone moiety of 3-oxabicyclo[3.1.0]hexan-2-ones
Fillion, E
Beingessner, RL
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24): : 9485 - 9488

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