Carbon-Fluorine Bond Formation for the Synthesis of Aryl Fluorides

被引：186

作者：

Furuya, Takeru ^{[1
]}

Klein, Johannes E. M. N. ^{[1
]}

Ritter, Tobias ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2010年 / 11期

关键词：

carbon-fluorine bond formation; transition metals; palladium; silver; catalysis; FORMING REDUCTIVE ELIMINATION; ENANTIOSELECTIVE VINYLOGOUS MANNICH; TRIMETHOXYSILYL ENOL ETHERS; SAKURAI-HOSOMI ALLYLATION; ASYMMETRIC ALDOL REACTION; CROSS-COUPLING REACTIONS; HIGHLY-ACTIVE CATALYST; ELECTROPHILIC FLUORINATION; C-O; OXIDATIVE ADDITION;

D O I：

10.1055/s-0029-1218742

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selection of carbon-fluorine bond-forming reactions is presented with particular focus on transition-metal-mediated fluorination. A brief summary of conventional fluorination reactions is followed by a discussion of fluorination reactions mediated by palladium and silver. Investigations into the mechanism as well as the conceptual difficulty associated with transition-metal-mediated carbon-fluorine bond formation are presented.

引用

页码：1804 / 1821

页数：18

共 182 条

[21] Fluorine in medicinal chemistry
Böhm, HJ
Banner, D
Bendels, S
Kansy, M
Kuhn, B
Müller, K
Obst-Sander, U
Stahl, M
[J]. CHEMBIOCHEM, 2004, 5 (05) : 637 - 643
[22] VAN DER WAALS VOLUMES + RADII
BONDI, A
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) : 441 - +
[23] Transition-Metal-Mediated Reactions for Csp2-F Bond Construction: The State of Play
Brown, John M.
Gouverneur, Veronique
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) : 8610 - 8614
[24] 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
[25] Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
Burgos, Carlos H.
Barder, Timothy E.
Huang, Xiaohua
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4321 - 4326
[26] REACTIVITY AND MECHANISM IN OXIDATIVE ADDITION TO PALLADIUM(II) AND REDUCTIVE ELIMINATION FROM PALLADIUM(IV) AND AN ESTIMATE OF THE PALLADIUM-METHYL BOND-ENERGY
BYERS, PK
CANTY, AJ
CRESPO, M
PUDDEPHATT, RJ
SCOTT, JD
[J]. ORGANOMETALLICS, 1988, 7 (06) : 1363 - 1367
[27] FLUORO-COMPLEXES OF PLATINUM METALS
CAIRNS, MA
DIXON, KR
MCFARLAND, JJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1975, (12): : 1159 - 1164
[28] Redox behavior of an organometallic palladium(II)/palladium(IV) system.: A new method for the synthesis of cationic palladium(IV) complexes
Campora, J
Palma, P
del Río, D
López, JA
Alvarez, E
Connelly, NG
[J]. ORGANOMETALLICS, 2005, 24 (15) : 3624 - 3628
[29] SYNTHESIS AND CHARACTERIZATION OF AMBIENT-TEMPERATURE STABLE ORGANOPALLADIUM(IV) COMPLEXES, INCLUDING ARYL, ETA(1)-ALLYL, ETHYLPALLADIUM(IV), AND PALLADA(IV)CYCLOPENTANE COMPLEXES - STRUCTURES OF THE POLY(PYRAZOL-1-YL)BORATE COMPLEXES PDME(3)((PZ)(3)BH) AND PDME(3)((PZ)(4)B) AND 3 POLYMORPHS OF PDME(2)ET((PZ)(3)BH)
CANTY, AJ
JIN, H
ROBERTS, AS
SKELTON, BW
TRAILL, PR
WHITE, AH
[J]. ORGANOMETALLICS, 1995, 14 (01) : 199 - 206
[30] Carbon-oxygen bond formation at metal(IV) centers:: Reactivity of palladium(II) and platinum(II) complexes of the [2,6-(dimethylaminomethyl)phenyl-N,C,N]-(pincer) ligand toward iodomethane and dibenzoyl peroxide;: Structural studies of M(II) and M(IV) complexes
Canty, AJ
Denney, MC
van Koten, G
Skelton, BW
White, AH
[J]. ORGANOMETALLICS, 2004, 23 (23) : 5432 - 5439

← 1 2 3 4 5 6 7 8 9 10 →