Palladium(III)-Catalyzed Fluorination of Arylboronic Acid Derivatives

被引：129

作者：

Mazzotti, Anthony R. ^{[1
]}

Campbell, Michael G. ^{[1
]}

Tang, Pingping ^{[1
]}

Murphy, Jennifer M. ^{[1
]}

Ritter, Tobias ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 38期

基金：

美国国家科学基金会;

关键词：

COPPER-MEDIATED FLUORINATION; C-H FLUORINATION; REDUCTIVE ELIMINATION; ELECTROPHILIC FLUORINATION; PD(III); DEOXYFLUORINATION; CONVERSION; MECHANISM;

D O I：

10.1021/ja405919z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical, palladium-catalyzed synthesis of aryl fluorides from arylboronic acid derivatives is presented. The reaction is operationally simple and amenable to multigram-scale synthesis. Evaluation of the reaction mechanism suggests a single-electron-transfer pathway, involving a Pd(III) intermediate that has been isolated and characterized.

引用

页码：14012 / 14015

页数：4

共 41 条

[1] 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

[2]

Campbell MG, 2011, NAT CHEM, V3, P949, DOI [10.1038/nchem.1197, 10.1038/NCHEM.1197]

[3] Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a Practical Auxiliary: A Weak-Coordination Approach [J].

Chan, Kelvin S. L. ;

Wasa, Masayuki ;

Wang, Xisheng ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9081-9084

[4] A Dinuclear Palladium Catalyst for α-Hydroxylation of Carbonyls with O2 [J].

Chuang, Gary Jing ;

Wang, Weike ;

Lee, Eunsung ;

Ritter, Tobias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) :1760-1762

[5] 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

[6] Copper-Mediated Fluorination of Aryl Iodides [J].

Fier, Patrick S. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) :10795-10798

[7] 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-+

[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

← 1 2 3 4 5 →