Copper-Mediated Oxidative Fluorination of Aryl Stannanes with Fluoride

被引：43
作者：
Gamache, Raymond F. [1 ]
Waldmann, Christopher [2 ,3 ]
Murphy, Jennifer M. [2 ,3 ]
机构：
[1] Univ Calif Los Angeles, Dept Chem & Biochem, 607 Charles E Young Dr East, Los Angeles, CA 90095 USA
[2] Univ Calif Los Angeles, David Geffen Sch Med, Dept Mol & Med Pharmacol, 570 Westwood Plaza, Los Angeles, CA 90095 USA
[3] Univ Calif Los Angeles, David Geffen Sch Med, Crump Inst Mol Imaging, 570 Westwood Plaza, Los Angeles, CA 90095 USA
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 18期
关键词：
CATALYZED FLUORINATION; NUCLEOPHILIC FLUORINATION; BORONIC ACIDS; BROMIDES; ARENES; BONDS; PET;
D O I：
10.1021/acs.orglett.6b02125
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regiospecific method for the oxidative fluorination of aryl stannanes using tetrabutylammonium triphenyldifluorosilicate (TBAT) and copper(II) triflate is described. This reaction is robust, uses readily available reagents, and proceeds via a stepwise protocol under mild conditions (60 degrees C, 3.2 h). Broad functional group tolerance, including arenes containing protic and nucleophilic groups, is demonstrated.
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收藏
页码：4522 / 4525
页数：4
相关论文
共 36 条
[1]   Synthesis of 4-fluorophenols from 4-tert-butylphenols and fluoride sources under oxidative conditions [J].
Bienvenu, A ;
Barthelemy, A ;
Boichut, S ;
Marquet, B ;
Billard, T ;
Langlois, BR .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2002, 67 (10) :1467-1478
[2]   Transition-Metal-Mediated Reactions for Csp2-F Bond Construction: The State of Play [J].
Brown, John M. ;
Gouverneur, Veronique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) :8610-8614
[3]   Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].
Campbell, Michael G. ;
Ritter, Tobias .
CHEMICAL REVIEWS, 2015, 115 (02) :612-633
[4]   Nucleophilic Aryl Fluorination and Aryl Halide Exchange Mediated by a CuI/CuIII Catalytic Cycle [J].
Casitas, Alicia ;
Canta, Merce ;
Sola, Miquel ;
Costas, Miguel ;
Ribas, Xavi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (48) :19386-19392
[5]   Selective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction [J].
Fier, Patrick S. ;
Hartwig, John F. .
SCIENCE, 2013, 342 (6161) :956-960
[6]   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
[7]   Copper-Mediated Fluorination of Aryl Iodides [J].
Fier, Patrick S. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) :10795-10798
[8]   Catalysis for fluorination and trifluoromethylation [J].
Furuya, Takeru ;
Kamlet, Adam S. ;
Ritter, Tobias .
NATURE, 2011, 473 (7348) :470-477
[9]   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
[10]   Palladium-mediated fluorination of arylboronic acids [J].
Furuya, Takeru ;
Kaiser, Hanns Martin ;
Ritter, Tobias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (32) :5993-5996
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