Transition-Metal-Mediated Reactions for Csp2-F Bond Construction: The State of Play

被引：96

作者：

Brown, John M. ^{[1
]}

Gouverneur, Veronique ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 46期

关键词：

alkenes; arenes; homogeneous catalysis; fluorine; transition metals; FORMING REDUCTIVE ELIMINATION; ARYLPALLADIUM(II) HALIDE-COMPLEXES; POSITRON-EMISSION-TOMOGRAPHY; PALLADIUM(IV) COMPLEXES; CESIUM FLUOROXYSULFATE; ACETYL HYPOFLUORITE; ARYLBORONIC ACIDS; ARYL FLUORIDES; C-O; FLUORINATION;

D O I：

10.1002/anie.200902121

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

It's a rate thing: Crucial conceptual advances have allowed for the development of a Pd-mediated pathway to Caryl-F by using either electrophilic (right) or nucleophilic (left) fluorinating reagents. Of significance is the recognition that PdIV intermediates reduce the barrier to C-F reductive elimination and the use of an ancillary bulky ligand to force reductive elimination from a 14-electron PdII complex. © 2009 Wiley-VCH Verlag GmbH &. Co. KGaA.

引用

页码：8610 / 8614

页数：5

共 42 条

[1] FLUORINATION OF AROMATIC-COMPOUNDS WITH F2 AND ACETYL HYPOFLUORITE - SYNTHESIS OF F-18-ARYL FLUORIDES BY CLEAVAGE OF ARYL-TIN BONDS
ADAM, MJ
RUTH, TJ
JIVAN, S
PATE, BD
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1984, 25 (03) : 329 - 337
[2] Reversible C-F bond formation and the Au-catalyzed hydrofluorination of alkynes
Akana, Jennifer A.
Bhattacharyya, Koyel X.
Mueller, Peter
Sadighi, Joseph P.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) : 7736 - +
[3] [Anonymous], ANGEW CHEM
[4] Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex
Ball, Nicholas D.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) : 3796 - +
[5] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products
Begue, Jean-Pierre
Bonnet-Delpon, Daniele
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) : 992 - 1012
[6] ELECTROPHILIC FLUORINATION OF ARYLTRIALKYLTIN DERIVATIVES WITH CESIUM FLUOROXYSULFATE
BRYCE, MR
CHAMBERS, RD
MULLINS, ST
PARKIN, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (21) : 1623 - 1624
[7] Chemistry with [18F]fluoride ion
Cai, Lisheng
Lu, Shuiyu
Pike, Victor W.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (17) : 2853 - 2873
[8] DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS
CANTY, AJ
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) : 83 - 90
[9] Catalytic multistep reactions via palladacycles
Catellani, M
[J]. SYNLETT, 2003, (03) : 298 - 313
[10] REGIOSPECIFIC AROMATIC FLUORODEMETALLATION OF GROUP-IVB METALLOARENES USING ELEMENTAL FLUORINE OR ACETYL HYPOFLUORITE
COENEN, HH
MOERLEIN, SM
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1987, 36 (01) : 63 - 75

← 1 2 3 4 5 →