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Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies
被引:306
作者
:
Billingsley, Kelvin 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
Billingsley, Kelvin L.
[
1
]
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.
[
1
]
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.
[
1
]
机构
:
[1]
MIT, Dept Chem, Cambridge, MA 02139 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2007年
/ 46卷
/ 28期
关键词
:
boronate esters;
borylation;
C-C coupling;
palladium;
Suzuki-Miyaura coupling;
D O I
:
10.1002/anie.200701551
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) From chloride to boronate: Catalysts comprising palladium and biaryl monophosphine ligands provide highly active systems for the borylation of aryl and heteroaryl chlorides (see scheme). Symmetrical and unsymmetrical biaryl products can also be prepared directly from two aryl chlorides without isolation of the intermediate boronate esters. Computational studies provide insight into the roles of the biaryl phosphine ligand and the KOAc base in the catalytic cycle. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5359 / 5363
页数:5
相关论文
共 27 条
[1]
[Anonymous], 2002, J ORGANOMET CHEM
[2]
Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
Barder, TE
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, TE
Walker, SD
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
Walker, SD
Martinelli, JR
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
Martinelli, JR
Buchwald, SL
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, SL
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
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BARDER TE, UNPUB
[4]
Structural insights into active catalyst structures and oxidative addition to (biaryl)phosphine - Palladium complexes via density functional theory and experimental studies
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.
Biscoe, Mark R.
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
Biscoe, Mark R.
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].
ORGANOMETALLICS,
2007,
26
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2192
[5]
Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls
Baudoin, O
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
Baudoin, O
Guénard, D
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
Guénard, D
Guéritte, F
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
Guéritte, F
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2000,
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DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Queen's University, Kingston
BECKE, AD
[J].
JOURNAL OF CHEMICAL PHYSICS,
1993,
98
(07)
: 5648
-
5652
[7]
Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis
Broutin, PE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Broutin, PE
Cerna, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Cerna, I
论文数:
引用数:
h-index:
机构:
Campaniello, M
Leroux, F
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Leroux, F
Colobert, F
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Colobert, F
[J].
ORGANIC LETTERS,
2004,
6
(24)
: 4419
-
4422
[8]
Frisch M. J., GAUSSIAN03 REVISION
[9]
Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system
Fürstner, A
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Fürstner, A
Seidel, G
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Seidel, G
[J].
ORGANIC LETTERS,
2002,
4
(04)
: 541
-
543
[10]
One pot biaryl synthesis via in situ boronate formation
Giroux, A
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Medicinal Chemistry, Merck-Frosst Ctr. Therapeut. Res., Pointe-Claire-Dorval, Que. H9R 4P8
Giroux, A
Han, YX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Medicinal Chemistry, Merck-Frosst Ctr. Therapeut. Res., Pointe-Claire-Dorval, Que. H9R 4P8
Han, YX
Prasit, P
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Medicinal Chemistry, Merck-Frosst Ctr. Therapeut. Res., Pointe-Claire-Dorval, Que. H9R 4P8
Prasit, P
[J].
TETRAHEDRON LETTERS,
1997,
38
(22)
: 3841
-
3844
←
1
2
3
→
共 27 条
[1]
[Anonymous], 2002, J ORGANOMET CHEM
[2]
Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
Barder, TE
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, TE
Walker, SD
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
Walker, SD
Martinelli, JR
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
Martinelli, JR
Buchwald, SL
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, SL
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(13)
: 4685
-
4696
[3]
BARDER TE, UNPUB
[4]
Structural insights into active catalyst structures and oxidative addition to (biaryl)phosphine - Palladium complexes via density functional theory and experimental studies
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.
Biscoe, Mark R.
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
Biscoe, Mark R.
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].
ORGANOMETALLICS,
2007,
26
(09)
: 2183
-
2192
[5]
Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls
Baudoin, O
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
Baudoin, O
Guénard, D
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
Guénard, D
Guéritte, F
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
Guéritte, F
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2000,
65
(26)
: 9268
-
9271
[6]
DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Queen's University, Kingston
BECKE, AD
[J].
JOURNAL OF CHEMICAL PHYSICS,
1993,
98
(07)
: 5648
-
5652
[7]
Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis
Broutin, PE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Broutin, PE
Cerna, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Cerna, I
论文数:
引用数:
h-index:
机构:
Campaniello, M
Leroux, F
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Leroux, F
Colobert, F
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France
Colobert, F
[J].
ORGANIC LETTERS,
2004,
6
(24)
: 4419
-
4422
[8]
Frisch M. J., GAUSSIAN03 REVISION
[9]
Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system
Fürstner, A
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Fürstner, A
Seidel, G
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Seidel, G
[J].
ORGANIC LETTERS,
2002,
4
(04)
: 541
-
543
[10]
One pot biaryl synthesis via in situ boronate formation
Giroux, A
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Medicinal Chemistry, Merck-Frosst Ctr. Therapeut. Res., Pointe-Claire-Dorval, Que. H9R 4P8
Giroux, A
Han, YX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Medicinal Chemistry, Merck-Frosst Ctr. Therapeut. Res., Pointe-Claire-Dorval, Que. H9R 4P8
Han, YX
Prasit, P
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Medicinal Chemistry, Merck-Frosst Ctr. Therapeut. Res., Pointe-Claire-Dorval, Que. H9R 4P8
Prasit, P
[J].
TETRAHEDRON LETTERS,
1997,
38
(22)
: 3841
-
3844
←
1
2
3
→