Palladium(III)-Catalyzed Fluorination of Arylboronic Acid Derivatives

被引：128

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 50 条

[41] A Palladium-Catalyzed Carbonylation Approach to Acid Chloride Synthesis
Quesnel, Jeffrey S.
Arndtsen, Bruce A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (45) : 16841 - 16844
[42] Palladium-Catalyzed Decarbonylative Nucleophilic Halogenation of Acid Anhydrides
Tian, Tian
Uei, Shuhei
Yan, Weidan
Nishihara, Yasushi
CATALYSTS, 2025, 15 (02)
[43] Palladium-Catalyzed Reduction of Acid Chlorides to Aldehydes with Hydrosilanes
Fujihara, Tetsuaki
Cong, Cong
Iwai, Tomohiro
Terao, Jun
Tsuji, Yasushi
SYNLETT, 2012, (16) : 2389 - 2392
[44] Catalytic cycle and off-cycle steps in the palladium-catalyzed fluorination of aryl bromide with biaryl monophosphine ligands: Theoretical free energy profile
Pliego Jr, Josefredo R.
MOLECULAR CATALYSIS, 2021, 506
[45] Cyclometalated Ir(III) complexes-catalyzed aerobic hydroxylation of arylboronic acids induced by visible-light
Yu, Hongcui
Liu, Chun
Dai, Xiaomei
Wang, Jing
Qiu, Jieshan
TETRAHEDRON, 2017, 73 (21) : 3031 - 3035
[46] Oxidative functionalization of naphthalene derivatives catalyzed by Mn (III)-porphyrins
Ge, Yunfei
Su, Xingxing
Li, Guijie
Yang, Yun-Fang
She, Yuanbin
TETRAHEDRON LETTERS, 2023, 123
[47] Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes
Newman, Stephen G.
Howell, Jennifer K.
Nicolaus, Norman
Lautens, Mark
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (38) : 14916 - 14919
[48] Palladium-Catalyzed Aerobic Oxidative Dehydrogenation of Cyclohexenes to Substituted Arene Derivatives
Iosub, Andrei V.
Stahl, Shannon S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (10) : 3454 - 3457
[49] Diphenyliodonium-Catalyzed Fluorination of Arynes: Synthesis of ortho-Fluoroiodoarenes
Zeng, Yuwen
Li, Guangyu
Hu, Jinbo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (37) : 10773 - 10777
[50] Depolymerization of Cellulose in Water Catalyzed by Phenylboronic Acid Derivatives
Levi, Noam
Khenkin, Alexander M.
Hailegnaw, Bekele
Neumann, Ronny
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (10): : 5799 - 5803

← 1 2 3 4 5 →