Pd(OAc)2-catalyzed regioselective aromatic C-H bond fluorination

被引:86
作者
Lou, Shao-Jie [1 ]
Xu, Dan-Qian [1 ]
Xia, Ai-Bao [1 ]
Wang, Yi-Feng [1 ]
Liu, Yun-Kui [1 ]
Du, Xiao-Hua [1 ]
Xu, Zhen-Yuan [1 ]
机构
[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Catalyt Hydrogenat Res Ctr, Hangzhou 310014, Zhejiang, Peoples R China
关键词
COPPER-MEDIATED FLUORINATION; REGIOSPECIFIC SYNTHESIS; REDUCTIVE ELIMINATION; ELECTROSPRAY MASS; ARYL; FUNCTIONALIZATION; MECHANISM; CATALYSIS;
D O I
10.1039/c3cc42220h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel Pd(OAc)(2)-NFSI-TFA system was developed for the highly selective ortho-monofluorination directed by diverse aryl-N-heterocyclic directing groups e. g., quinoxaline, pyrazole, benzo[d]oxazole, and pyrazine derivatives. A Pd(II/IV) catalytic cycle was proposed based on the ESI-MS/MS studies.
引用
收藏
页码:6218 / 6220
页数:3
相关论文
共 42 条
[11]   Copper-Mediated Fluorination of Arylboronate Esters. Identification of a Copper(III) Fluoride Complex [J].
Fier, Patrick S. ;
Luo, Jingwei ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (07) :2552-2559
[12]   Copper-Mediated Fluorination of Aryl Iodides [J].
Fier, Patrick S. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) :10795-10798
[13]   Carbon-fluorine reductive elimination from a high-valent palladium fluoride [J].
Furuya, Takeru ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10060-+
[14]   Catalysis for fluorination and trifluoromethylation [J].
Furuya, Takeru ;
Kamlet, Adam S. ;
Ritter, Tobias .
NATURE, 2011, 473 (7348) :470-477
[15]   Carbon-Fluorine Bond Formation for the Synthesis of Aryl Fluorides [J].
Furuya, Takeru ;
Klein, Johannes E. M. N. ;
Ritter, Tobias .
SYNTHESIS-STUTTGART, 2010, (11) :1804-1821
[16]   Palladium-mediated fluorination of arylboronic acids [J].
Furuya, Takeru ;
Kaiser, Hanns Martin ;
Ritter, Tobias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (32) :5993-5996
[17]   Mechanism of C-F Reductive Elimination from Palladium(IV) Fluorides [J].
Furuya, Takeru ;
Benitez, Diego ;
Tkatchouk, Ekaterina ;
Strom, Alexandra E. ;
Tang, Pingping ;
Goddard, William A., III ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3793-3807
[18]   Fluorination of Boronic Acids Mediated by Silver(I) Triflate [J].
Furuya, Takeru ;
Ritter, Tobias .
ORGANIC LETTERS, 2009, 11 (13) :2860-2863
[19]   Silver-Mediated Fluorination of Functionalized Aryl Stannanes [J].
Furuya, Takeru ;
Strom, Alexandra E. ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) :1662-+
[20]   Snapshot of the Palladium(II)-Catalyzed Oxidative Biaryl Bond Formation by X-ray Analysis of the Intermediate Diaryl Palladium(II) Complex [J].
Gensch, Tobias ;
Roennefahrt, Marika ;
Czerwonka, Regina ;
Jaeger, Anne ;
Kataeva, Olga ;
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (03) :770-776