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CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds
被引:502
作者
:
Li, ZP
论文数:
0
引用数:
0
h-index:
0
机构:
McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
Li, ZP
[
1
]
Li, CJ
论文数:
0
引用数:
0
h-index:
0
机构:
McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
Li, CJ
[
1
]
机构
:
[1]
McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2005年
/ 127卷
/ 19期
关键词
:
D O I
:
10.1021/ja0516054
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
A novel and efficient C-C bond formation method was developed via the cross-dehydrogenative coupling (CDC) reaction of indoles and tetrahydroisoquinolines catalyzed by copper bromide in the presence of an oxidizing reagent, tert-BuOOH. The CDC reaction provides a simple and efficient catalytic method to construct indolyl tetrahydroisoquinolines via a combination of sp3 C-H bond and sp2 C-H bond followed by C-C bond formation. Copyright © 2005 American Chemical Society.
引用
收藏
页码:6968 / 6969
页数:2
相关论文
共 35 条
[1]
Anastas P. T., 1998, GREEN CHEM THEORY PR
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Direct coupling of pyrroles with carbonyl compounds: Short enantioselective synthesis of (S)-Ketorolac
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Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Baran, PS
;
Richter, JM
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0
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0
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Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Richter, JM
;
Lin, DW
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0
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0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Lin, DW
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
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β-Phenylethylamines and the isoquinoline alkaloids
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Bentley, KW
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β-phenylethylamines and the isoquinoline alkaloids
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Bentley, KW
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Marrview, Tillybirloch, Midmar, Aberdeenshire
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BROWN, SH
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0
h-index:
0
机构:
YALE UNIV,STERLING CHEM LAB,NEW HAVEN,CT 06520
YALE UNIV,STERLING CHEM LAB,NEW HAVEN,CT 06520
BROWN, SH
;
CRABTREE, RH
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0
h-index:
0
机构:
YALE UNIV,STERLING CHEM LAB,NEW HAVEN,CT 06520
YALE UNIV,STERLING CHEM LAB,NEW HAVEN,CT 06520
CRABTREE, RH
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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Asymmetric synthesis of isoquinoline alkaloids
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Chrzanowska, M
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Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
Chrzanowska, M
;
Rozwadowska, MD
论文数:
0
引用数:
0
h-index:
0
机构:
Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
Rozwadowska, MD
.
CHEMICAL REVIEWS,
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Cross-coupling of sp3 C-H bonds and alkenes:: Catalytic cyclization of alkene-amide substrates
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DeBoef, B
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Columbia Univ, Dept Chem, New York, NY 10027 USA
Columbia Univ, Dept Chem, New York, NY 10027 USA
DeBoef, B
;
Pastine, SJ
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0
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0
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0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA
Columbia Univ, Dept Chem, New York, NY 10027 USA
Pastine, SJ
;
Sames, D
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0
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0
h-index:
0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA
Columbia Univ, Dept Chem, New York, NY 10027 USA
Sames, D
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
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:6556
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Enantioselective, copper(I)-catalyzed three-component reaction for the preparation of propargylamines
[J].
Gommermann, N
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem, D-81377 Munich, Germany
Univ Munich, Dept Chem, D-81377 Munich, Germany
Gommermann, N
;
Koradin, X
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem, D-81377 Munich, Germany
Univ Munich, Dept Chem, D-81377 Munich, Germany
Koradin, X
;
Polborn, K
论文数:
0
引用数:
0
h-index:
0
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Univ Munich, Dept Chem, D-81377 Munich, Germany
Univ Munich, Dept Chem, D-81377 Munich, Germany
Polborn, K
;
Knochel, P
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引用数:
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h-index:
0
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Univ Munich, Dept Chem, D-81377 Munich, Germany
Univ Munich, Dept Chem, D-81377 Munich, Germany
Knochel, P
.
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2003,
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Oxidative cross-coupling of acrylates with vinyl carboxylates catalyzed by a Pd(OAc)2/HPMoV/O2 system
[J].
Hatamoto, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
Hatamoto, Y
;
Sakaguchi, S
论文数:
0
引用数:
0
h-index:
0
机构:
Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
Sakaguchi, S
;
论文数:
引用数:
h-index:
机构:
Ishii, Y
.
ORGANIC LETTERS,
2004,
6
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:4623
-4625
[10]
Catalytic functionalization of arenes and alkanes via C-H bond activation
[J].
Jia, CG
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Jia, CG
;
Kitamura, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Kitamura, T
;
Fujiwara, Y
论文数:
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引用数:
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h-index:
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Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Fujiwara, Y
.
ACCOUNTS OF CHEMICAL RESEARCH,
2001,
34
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:633
-639
←
1
2
3
4
→
共 35 条
[1]
Anastas P. T., 1998, GREEN CHEM THEORY PR
[2]
Direct coupling of pyrroles with carbonyl compounds: Short enantioselective synthesis of (S)-Ketorolac
[J].
Baran, PS
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Baran, PS
;
Richter, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Richter, JM
;
Lin, DW
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Lin, DW
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(04)
:609
-612
[3]
β-Phenylethylamines and the isoquinoline alkaloids
[J].
Bentley, KW
论文数:
0
引用数:
0
h-index:
0
Bentley, KW
.
NATURAL PRODUCT REPORTS,
2005,
22
(02)
:249
-268
[4]
β-phenylethylamines and the isoquinoline alkaloids
[J].
Bentley, KW
论文数:
0
引用数:
0
h-index:
0
机构:
Marrview, Tillybirloch, Midmar, Aberdeenshire
Bentley, KW
.
NATURAL PRODUCT REPORTS,
2004,
21
(03)
:395
-424
[5]
MAKING MERCURY-PHOTOSENSITIZED DEHYDRODIMERIZATION INTO AN ORGANIC SYNTHETIC METHOD - VAPOR-PRESSURE SELECTIVITY AND THE BEHAVIOR OF FUNCTIONALIZED SUBSTRATES
[J].
BROWN, SH
论文数:
0
引用数:
0
h-index:
0
机构:
YALE UNIV,STERLING CHEM LAB,NEW HAVEN,CT 06520
YALE UNIV,STERLING CHEM LAB,NEW HAVEN,CT 06520
BROWN, SH
;
CRABTREE, RH
论文数:
0
引用数:
0
h-index:
0
机构:
YALE UNIV,STERLING CHEM LAB,NEW HAVEN,CT 06520
YALE UNIV,STERLING CHEM LAB,NEW HAVEN,CT 06520
CRABTREE, RH
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1989,
111
(08)
:2935
-2946
[6]
Asymmetric synthesis of isoquinoline alkaloids
[J].
Chrzanowska, M
论文数:
0
引用数:
0
h-index:
0
机构:
Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
Chrzanowska, M
;
Rozwadowska, MD
论文数:
0
引用数:
0
h-index:
0
机构:
Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
Rozwadowska, MD
.
CHEMICAL REVIEWS,
2004,
104
(07)
:3341
-3370
[7]
Cross-coupling of sp3 C-H bonds and alkenes:: Catalytic cyclization of alkene-amide substrates
[J].
DeBoef, B
论文数:
0
引用数:
0
h-index:
0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA
Columbia Univ, Dept Chem, New York, NY 10027 USA
DeBoef, B
;
Pastine, SJ
论文数:
0
引用数:
0
h-index:
0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA
Columbia Univ, Dept Chem, New York, NY 10027 USA
Pastine, SJ
;
Sames, D
论文数:
0
引用数:
0
h-index:
0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA
Columbia Univ, Dept Chem, New York, NY 10027 USA
Sames, D
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(21)
:6556
-6557
[8]
Enantioselective, copper(I)-catalyzed three-component reaction for the preparation of propargylamines
[J].
Gommermann, N
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem, D-81377 Munich, Germany
Univ Munich, Dept Chem, D-81377 Munich, Germany
Gommermann, N
;
Koradin, X
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem, D-81377 Munich, Germany
Univ Munich, Dept Chem, D-81377 Munich, Germany
Koradin, X
;
Polborn, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem, D-81377 Munich, Germany
Univ Munich, Dept Chem, D-81377 Munich, Germany
Polborn, K
;
Knochel, P
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Munich, Dept Chem, D-81377 Munich, Germany
Univ Munich, Dept Chem, D-81377 Munich, Germany
Knochel, P
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2003,
42
(46)
:5763
-5766
[9]
Oxidative cross-coupling of acrylates with vinyl carboxylates catalyzed by a Pd(OAc)2/HPMoV/O2 system
[J].
Hatamoto, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
Hatamoto, Y
;
Sakaguchi, S
论文数:
0
引用数:
0
h-index:
0
机构:
Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
Sakaguchi, S
;
论文数:
引用数:
h-index:
机构:
Ishii, Y
.
ORGANIC LETTERS,
2004,
6
(24)
:4623
-4625
[10]
Catalytic functionalization of arenes and alkanes via C-H bond activation
[J].
Jia, CG
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Jia, CG
;
Kitamura, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Kitamura, T
;
Fujiwara, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Kyushu Univ, Fac Engn, Dept Appl Chem, Fukuoka 8128581, Japan
Fujiwara, Y
.
ACCOUNTS OF CHEMICAL RESEARCH,
2001,
34
(08)
:633
-639
←
1
2
3
4
→