共 46 条
Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C
被引:114
作者:

Felpin, FX
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机构:
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
机构:
[1] Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
关键词:
D O I:
10.1021/jo051501b
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The first Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(O)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 degrees C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(O)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.
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页码:8575 / 8578
页数:4
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共 46 条
[1]
A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants
[J].
Arcadi, A
;
Cerichelli, G
;
Chiarini, M
;
Correa, M
;
Zorzan, D
.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2003, 2003 (20)
:4080-4086

Arcadi, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy

Cerichelli, G
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy

Chiarini, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy

Correa, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy

Zorzan, D
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy
[2]
Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling
[J].
Arvela, RK
;
Leadbeater, NE
.
ORGANIC LETTERS,
2005, 7 (11)
:2101-2104

Arvela, RK
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Connecticut, Dept Chem, Unit 3060, Storrs, CT 06269 USA Univ Connecticut, Dept Chem, Unit 3060, Storrs, CT 06269 USA

Leadbeater, NE
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Connecticut, Dept Chem, Unit 3060, Storrs, CT 06269 USA Univ Connecticut, Dept Chem, Unit 3060, Storrs, CT 06269 USA
[3]
Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations
[J].
Badone, D
;
Baroni, M
;
Cardamone, R
;
Ielmini, A
;
Guzzi, U
.
JOURNAL OF ORGANIC CHEMISTRY,
1997, 62 (21)
:7170-7173

Badone, D
论文数: 0 引用数: 0
h-index: 0
机构: Research Center Sanofi-Midy, 38 20137 Milan, via Piranesi

Baroni, M
论文数: 0 引用数: 0
h-index: 0
机构: Research Center Sanofi-Midy, 38 20137 Milan, via Piranesi

Cardamone, R
论文数: 0 引用数: 0
h-index: 0
机构: Research Center Sanofi-Midy, 38 20137 Milan, via Piranesi

Ielmini, A
论文数: 0 引用数: 0
h-index: 0
机构: Research Center Sanofi-Midy, 38 20137 Milan, via Piranesi

Guzzi, U
论文数: 0 引用数: 0
h-index: 0
机构: Research Center Sanofi-Midy, 38 20137 Milan, via Piranesi
[4]
Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
[J].
Barder, TE
;
Walker, SD
;
Martinelli, JR
;
Buchwald, SL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005, 127 (13)
:4685-4696

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

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

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

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
[5]
Microwave-assisted aqueous Suzuki cross-coupling reactions
[J].
Blettner, CG
;
König, WA
;
Stenzel, W
;
Schotten, T
.
JOURNAL OF ORGANIC CHEMISTRY,
1999, 64 (11)
:3885-3890

Blettner, CG
论文数: 0 引用数: 0
h-index: 0
机构: Lilly Forsch Hamburg, D-20253 Hamburg, Germany

König, WA
论文数: 0 引用数: 0
h-index: 0
机构: Lilly Forsch Hamburg, D-20253 Hamburg, Germany

Stenzel, W
论文数: 0 引用数: 0
h-index: 0
机构: Lilly Forsch Hamburg, D-20253 Hamburg, Germany

Schotten, T
论文数: 0 引用数: 0
h-index: 0
机构: Lilly Forsch Hamburg, D-20253 Hamburg, Germany
[6]
Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media
[J].
Bumagin, NA
;
Bykov, VV
.
TETRAHEDRON,
1997, 53 (42)
:14437-14450

Bumagin, NA
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Moscow State University, Moscow

Bykov, VV
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Moscow State University, Moscow
[7]
Effective heterogeneous palladium catalysis of the reactions of organoboron compounds with aryl halides
[J].
Bykov, VV
;
Bumagin, NA
.
RUSSIAN CHEMICAL BULLETIN,
1997, 46 (07)
:1344-1346

Bykov, VV
论文数: 0 引用数: 0
h-index: 0
机构:
MOSCOW MV LOMONOSOV STATE UNIV,DEPT CHEM,MOSCOW 119899,VOROBEVY GORY,RUSSIA MOSCOW MV LOMONOSOV STATE UNIV,DEPT CHEM,MOSCOW 119899,VOROBEVY GORY,RUSSIA

Bumagin, NA
论文数: 0 引用数: 0
h-index: 0
机构:
MOSCOW MV LOMONOSOV STATE UNIV,DEPT CHEM,MOSCOW 119899,VOROBEVY GORY,RUSSIA MOSCOW MV LOMONOSOV STATE UNIV,DEPT CHEM,MOSCOW 119899,VOROBEVY GORY,RUSSIA
[8]
Palladium-catalyzed functionalization of 5-and 7-azaindoles
[J].
Chi, SM
;
Choi, JK
;
Yum, EK
;
Chi, DY
.
TETRAHEDRON LETTERS,
2000, 41 (06)
:919-922

Chi, SM
论文数: 0 引用数: 0
h-index: 0
机构: Korea Res Inst Chem Technol, Bioorgan Sci Div, Yusung 305600, Taejeon, South Korea

Choi, JK
论文数: 0 引用数: 0
h-index: 0
机构: Korea Res Inst Chem Technol, Bioorgan Sci Div, Yusung 305600, Taejeon, South Korea

Yum, EK
论文数: 0 引用数: 0
h-index: 0
机构: Korea Res Inst Chem Technol, Bioorgan Sci Div, Yusung 305600, Taejeon, South Korea

Chi, DY
论文数: 0 引用数: 0
h-index: 0
机构: Korea Res Inst Chem Technol, Bioorgan Sci Div, Yusung 305600, Taejeon, South Korea
[9]
Suzuki-Miyaura cross-coupling with quasi-heterogeneous palladium
[J].
Conlon, DA
;
Pipik, B
;
Ferdinand, S
;
LeBlond, CR
;
Sowa, JR
;
Izzo, B
;
Collins, P
;
Ho, GJ
;
Williams, JM
;
Shi, YJ
;
Sun, YK
.
ADVANCED SYNTHESIS & CATALYSIS,
2003, 345 (08)
:931-935

Conlon, DA
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Pipik, B
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Ferdinand, S
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

LeBlond, CR
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Sowa, JR
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Izzo, B
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Collins, P
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Ho, GJ
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Williams, JM
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Shi, YJ
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

Sun, YK
论文数: 0 引用数: 0
h-index: 0
机构: Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
[10]
High-intensity ultrasound and microwave, alone or combined, promote Pd/C-catalyzed aryl-aryl couplings
[J].
Cravotto, G
;
Beggiato, M
;
Penoni, A
;
Palmisano, G
;
Tollari, S
;
Lévêque, JM
;
Bonrath, W
.
TETRAHEDRON LETTERS,
2005, 46 (13)
:2267-2271

Cravotto, G
论文数: 0 引用数: 0
h-index: 0
机构: Univ Insumbria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

Beggiato, M
论文数: 0 引用数: 0
h-index: 0
机构: Univ Insumbria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

Penoni, A
论文数: 0 引用数: 0
h-index: 0
机构: Univ Insumbria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

论文数: 引用数:
h-index:
机构:

Tollari, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Insumbria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

Lévêque, JM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Insumbria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

Bonrath, W
论文数: 0 引用数: 0
h-index: 0
机构: Univ Insumbria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy