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A New and Practical Grignard-Coupling-Fluorination Sequence: Synthesis of 2-Aryl Fluoroarenes
被引:17
作者
:
Anbarasan, Pazhamalai
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rostock, Katalyse eV, Leibniz Inst, D-18059 Rostock, Germany
Univ Rostock, Katalyse eV, Leibniz Inst, D-18059 Rostock, Germany
Anbarasan, Pazhamalai
[
1
]
Neumann, Helfried
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rostock, Katalyse eV, Leibniz Inst, D-18059 Rostock, Germany
Univ Rostock, Katalyse eV, Leibniz Inst, D-18059 Rostock, Germany
Neumann, Helfried
[
1
]
Beller, Matthias
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rostock, Katalyse eV, Leibniz Inst, D-18059 Rostock, Germany
Univ Rostock, Katalyse eV, Leibniz Inst, D-18059 Rostock, Germany
Beller, Matthias
[
1
]
机构
:
[1]
Univ Rostock, Katalyse eV, Leibniz Inst, D-18059 Rostock, Germany
来源
:
CHEMISTRY-AN ASIAN JOURNAL
|
2010年
/ 5卷
/ 08期
关键词
:
arylfluorides;
arynes;
domino reactions;
fluorination;
Grignard reaction;
ELECTROPHILIC FLUORINATION;
FUNCTIONALIZED ARYL;
EFFICIENT SYNTHESIS;
HIGHLY EFFICIENT;
REAGENTS;
MAGNESIUM;
SALTS;
ARYLMAGNESIUM;
SELECTFLUOR;
ELIMINATION;
D O I
:
10.1002/asia.201000288
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
A new strategy for the synthesis of 2-aryl-and 2-heteroaryl fluoroarenes has been developed. An intermolecular domino Grignard-coupling-fluorination sequence affords a range of 2-fluorobiaryls from aryl bromides under mild conditions. This methodology can be further extended to the synthesis of 2′-aryl-2-fluorobiphenyls. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1775 / 1778
页数:4
相关论文
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Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
Burgos, Carlos H.
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0
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0
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Burgos, Carlos H.
Barder, Timothy E.
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Barder, Timothy E.
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0
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0
h-index:
0
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Huang, Xiaohua
Buchwald, Stephen L.
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0
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0
h-index:
0
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Buchwald, Stephen L.
[J].
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2006,
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4326
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Metal-free electrophilic fluorination of alkyl trifluoroborates and boronic acids
Cazorla, Clement
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0
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0
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0
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Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Cazorla, Clement
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Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
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Metay, Estelle
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Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Andrioletti, Bruno
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0
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0
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Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Lemaire, Marc
[J].
TETRAHEDRON LETTERS,
2009,
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3938
[13]
SELECTIVE, ELECTROPHILIC FLUORINATIONS USING N-FLUORO-O-BENZENEDISULFONIMIDE
DAVIS, FA
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0
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0
h-index:
0
机构:
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
DAVIS, FA
HAN, W
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0
引用数:
0
h-index:
0
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DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
HAN, W
MURPHY, CK
论文数:
0
引用数:
0
h-index:
0
机构:
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
MURPHY, CK
[J].
JOURNAL OF ORGANIC CHEMISTRY,
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4737
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N-FLUORO-ORTHO-BENZENEDISULFONIMIDE - A USEFUL NEW FLUORINATING REAGENT
DAVIS, FA
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0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Drexel University, Philadelphia
DAVIS, FA
HAN, W
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0
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0
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0
机构:
Department of Chemistry, Drexel University, Philadelphia
HAN, W
[J].
TETRAHEDRON LETTERS,
1991,
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1634
[15]
NUCLEOPHILIC-SUBSTITUTION VERSUS ELECTRON-TRANSFER .2. SN2 AT FLUORINE AND ELECTRON-TRANSFER ARE COMPETING AND DIFFERENT PATHWAYS IN ELECTROPHILIC FLUORINATIONS
DIFFERDING, E
论文数:
0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
DIFFERDING, E
WEHRLI, M
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0
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0
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0
机构:
CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
WEHRLI, M
[J].
TETRAHEDRON LETTERS,
1991,
32
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: 3819
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3822
[16]
Two palladium-catalyzed domino reactions from one set of substrates/reagents:: Efficient synthesis of substituted indenes and cis-stilbenoid hydrocarbons from the same internal alkynes and hindered grignard reagents
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0
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0
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CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
Dong, Cheng-Guo
Yeung, Pik
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0
h-index:
0
机构:
CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
Yeung, Pik
Hu, Qiao-Sheng
论文数:
0
引用数:
0
h-index:
0
机构:
CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
Hu, Qiao-Sheng
[J].
ORGANIC LETTERS,
2007,
9
(02)
: 363
-
366
[17]
AROMATIC FLUORINE COMPOUNDS .7. REPLACEMENT OF AROMATIC -CL AND -NO2 GROUPS BY -F
FINGER, GC
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0
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0
h-index:
0
FINGER, GC
KRUSE, CW
论文数:
0
引用数:
0
h-index:
0
KRUSE, CW
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1956,
78
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: 6034
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6037
[18]
Furuya T., 2008, Angew. Chem, V120, P6082, DOI DOI 10.1002/ANGE.200802164
[19]
Carbon-fluorine reductive elimination from a high-valent palladium fluoride
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h-index:
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Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
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h-index:
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Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Ritter, Tobias
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2008,
130
(31)
: 10060
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+
[20]
Palladium-mediated fluorination of arylboronic acids
Furuya, Takeru
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0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
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Kaiser, Hanns Martin
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h-index:
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Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Kaiser, Hanns Martin
Ritter, Tobias
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引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Ritter, Tobias
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2008,
47
(32)
: 5993
-
5996
←
1
2
3
4
5
6
7
→
共 63 条
[11]
Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
Burgos, Carlos H.
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Burgos, Carlos H.
Barder, Timothy E.
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Barder, Timothy E.
Huang, Xiaohua
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Huang, Xiaohua
Buchwald, Stephen L.
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Buchwald, Stephen L.
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(26)
: 4321
-
4326
[12]
Metal-free electrophilic fluorination of alkyl trifluoroborates and boronic acids
Cazorla, Clement
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Cazorla, Clement
Metay, Estelle
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Metay, Estelle
Andrioletti, Bruno
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Andrioletti, Bruno
Lemaire, Marc
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
Lemaire, Marc
[J].
TETRAHEDRON LETTERS,
2009,
50
(27)
: 3936
-
3938
[13]
SELECTIVE, ELECTROPHILIC FLUORINATIONS USING N-FLUORO-O-BENZENEDISULFONIMIDE
DAVIS, FA
论文数:
0
引用数:
0
h-index:
0
机构:
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
DAVIS, FA
HAN, W
论文数:
0
引用数:
0
h-index:
0
机构:
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
HAN, W
MURPHY, CK
论文数:
0
引用数:
0
h-index:
0
机构:
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104
MURPHY, CK
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1995,
60
(15)
: 4730
-
4737
[14]
N-FLUORO-ORTHO-BENZENEDISULFONIMIDE - A USEFUL NEW FLUORINATING REAGENT
DAVIS, FA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Drexel University, Philadelphia
DAVIS, FA
HAN, W
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Drexel University, Philadelphia
HAN, W
[J].
TETRAHEDRON LETTERS,
1991,
32
(13)
: 1631
-
1634
[15]
NUCLEOPHILIC-SUBSTITUTION VERSUS ELECTRON-TRANSFER .2. SN2 AT FLUORINE AND ELECTRON-TRANSFER ARE COMPETING AND DIFFERENT PATHWAYS IN ELECTROPHILIC FLUORINATIONS
DIFFERDING, E
论文数:
0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
DIFFERDING, E
WEHRLI, M
论文数:
0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
WEHRLI, M
[J].
TETRAHEDRON LETTERS,
1991,
32
(31)
: 3819
-
3822
[16]
Two palladium-catalyzed domino reactions from one set of substrates/reagents:: Efficient synthesis of substituted indenes and cis-stilbenoid hydrocarbons from the same internal alkynes and hindered grignard reagents
Dong, Cheng-Guo
论文数:
0
引用数:
0
h-index:
0
机构:
CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
Dong, Cheng-Guo
Yeung, Pik
论文数:
0
引用数:
0
h-index:
0
机构:
CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
Yeung, Pik
Hu, Qiao-Sheng
论文数:
0
引用数:
0
h-index:
0
机构:
CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
Hu, Qiao-Sheng
[J].
ORGANIC LETTERS,
2007,
9
(02)
: 363
-
366
[17]
AROMATIC FLUORINE COMPOUNDS .7. REPLACEMENT OF AROMATIC -CL AND -NO2 GROUPS BY -F
FINGER, GC
论文数:
0
引用数:
0
h-index:
0
FINGER, GC
KRUSE, CW
论文数:
0
引用数:
0
h-index:
0
KRUSE, CW
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1956,
78
(23)
: 6034
-
6037
[18]
Furuya T., 2008, Angew. Chem, V120, P6082, DOI DOI 10.1002/ANGE.200802164
[19]
Carbon-fluorine reductive elimination from a high-valent palladium fluoride
Furuya, Takeru
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Furuya, Takeru
Ritter, Tobias
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Ritter, Tobias
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2008,
130
(31)
: 10060
-
+
[20]
Palladium-mediated fluorination of arylboronic acids
Furuya, Takeru
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Furuya, Takeru
Kaiser, Hanns Martin
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Kaiser, Hanns Martin
Ritter, Tobias
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Ritter, Tobias
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2008,
47
(32)
: 5993
-
5996
←
1
2
3
4
5
6
7
→