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Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones
被引:315
作者
:
论文数:
引用数:
h-index:
机构:
Bernini, Roberta
[
2
,
3
]
Fabrizi, Giancarlo
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
Fabrizi, Giancarlo
[
1
]
Sferrazza, Alessio
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
Sferrazza, Alessio
[
1
]
Cacchi, Sandro
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
Cacchi, Sandro
[
1
]
机构
:
[1]
Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
[2]
Univ Tuscia, Dipartimento ABAC, Viterbo, Italy
[3]
Consorzio Univ La Chim Ambiente, Viterbo, Italy
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2009年
/ 48卷
/ 43期
关键词
:
C-C coupling;
copper;
heterogeneous catalysis;
indoles;
synthesis design;
CONJUGATE REDUCTION;
DIRECT ARYLATIONS;
ACTIVATION;
AMINATION;
CYCLIZATION;
ANALOGS;
ESTERS;
D O I
:
10.1002/anie.200902440
中图分类号
:
O6 [化学];
学科分类号
:
070301
[无机化学]
;
摘要
:
A variety of functionalities, including the whole range of halogen substituents, are tolerated in the title reaction, an intramolecular approach for the construction of a multisubstituted indole skeleton from readily available enaminones (see scheme; phen=1,10-phenanthroline). The indole products are also prepared directly in high yield from α, β-ynones and primary amines. © 2009 Wiley-VCH Verlag.
引用
收藏
页码:8078 / 8081
页数:4
相关论文
共 53 条
[1]
Catalytic arylation reactions by C-H bond activation with aryl tosylates
[J].
Ackermann, L
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Ackermann, L
;
Althammer, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Althammer, A
;
Born, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Born, R
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(16)
:2619
-2622
[2]
Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations
[J].
Ackermann, Lutz
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Ackermann, Lutz
;
Mulzer, Michael
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Mulzer, Michael
.
ORGANIC LETTERS,
2008,
10
(21)
:5043
-5045
[3]
Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles
[J].
Ackermann, Lutz
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Ackermann, Lutz
;
Potukuchi, Harish K.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Potukuchi, Harish K.
;
Landsberg, Dirk
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Landsberg, Dirk
;
Vicente, Ruben
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Vicente, Ruben
.
ORGANIC LETTERS,
2008,
10
(14)
:3081
-3084
[4]
Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents
[J].
Ackermann, Lutz
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Ackermann, Lutz
;
Vicente, Ruben
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Vicente, Ruben
;
Althammer, Andreas
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Althammer, Andreas
.
ORGANIC LETTERS,
2008,
10
(11)
:2299
-2302
[5]
Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations
[J].
Ackermann, Lutz
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Ackermann, Lutz
.
SYNLETT,
2007,
(04)
:507
-526
[6]
Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
[J].
Alberico, Dino
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Alberico, Dino
;
Scott, Mark E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Scott, Mark E.
;
论文数:
引用数:
h-index:
机构:
Lautens, Mark
.
CHEMICAL REVIEWS,
2007,
107
(01)
:174
-238
[7]
Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
[J].
Alonso, F
论文数:
0
引用数:
0
h-index:
0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
Alonso, F
;
Beletskaya, IP
论文数:
0
引用数:
0
h-index:
0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
Beletskaya, IP
;
Yus, M
论文数:
0
引用数:
0
h-index:
0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
Yus, M
.
CHEMICAL REVIEWS,
2004,
104
(06)
:3079
-3159
[8]
[Anonymous], 2006, ANGEW CHEM
[9]
[Anonymous], 2008, ANGEW CHEM
[10]
Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst
[J].
Appella, DH
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
Appella, DH
;
Moritani, Y
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
Moritani, Y
;
Shintani, 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
Shintani, R
;
Ferreira, EM
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
Ferreira, EM
;
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
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(40)
:9473
-9474
←
1
2
3
4
5
6
→
共 53 条
[1]
Catalytic arylation reactions by C-H bond activation with aryl tosylates
[J].
Ackermann, L
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Ackermann, L
;
Althammer, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Althammer, A
;
Born, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Born, R
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(16)
:2619
-2622
[2]
Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations
[J].
Ackermann, Lutz
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Ackermann, Lutz
;
Mulzer, Michael
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Mulzer, Michael
.
ORGANIC LETTERS,
2008,
10
(21)
:5043
-5045
[3]
Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles
[J].
Ackermann, Lutz
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Ackermann, Lutz
;
Potukuchi, Harish K.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Potukuchi, Harish K.
;
Landsberg, Dirk
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Landsberg, Dirk
;
Vicente, Ruben
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Vicente, Ruben
.
ORGANIC LETTERS,
2008,
10
(14)
:3081
-3084
[4]
Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents
[J].
Ackermann, Lutz
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Ackermann, Lutz
;
Vicente, Ruben
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Vicente, Ruben
;
Althammer, Andreas
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
Althammer, Andreas
.
ORGANIC LETTERS,
2008,
10
(11)
:2299
-2302
[5]
Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations
[J].
Ackermann, Lutz
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
Ackermann, Lutz
.
SYNLETT,
2007,
(04)
:507
-526
[6]
Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
[J].
Alberico, Dino
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Alberico, Dino
;
Scott, Mark E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Scott, Mark E.
;
论文数:
引用数:
h-index:
机构:
Lautens, Mark
.
CHEMICAL REVIEWS,
2007,
107
(01)
:174
-238
[7]
Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
[J].
Alonso, F
论文数:
0
引用数:
0
h-index:
0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
Alonso, F
;
Beletskaya, IP
论文数:
0
引用数:
0
h-index:
0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
Beletskaya, IP
;
Yus, M
论文数:
0
引用数:
0
h-index:
0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
Yus, M
.
CHEMICAL REVIEWS,
2004,
104
(06)
:3079
-3159
[8]
[Anonymous], 2006, ANGEW CHEM
[9]
[Anonymous], 2008, ANGEW CHEM
[10]
Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst
[J].
Appella, DH
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
Appella, DH
;
Moritani, Y
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
Moritani, Y
;
Shintani, 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
Shintani, R
;
Ferreira, EM
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
Ferreira, EM
;
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
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(40)
:9473
-9474
←
1
2
3
4
5
6
→