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Synthesis of seven-membered-ring ketones by arylative ring expansion of alkyne-substituted cyclobutanones
被引:85
作者
:
Matsuda, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Matsuda, T
[
1
]
Makino, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Makino, M
[
1
]
Murakami, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Murakami, M
[
1
]
机构
:
[1]
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2005年
/ 44卷
/ 29期
关键词
:
rhodium;
boron;
elimination;
ketones;
ring expansion;
D O I
:
10.1002/anie.200500799
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) Ever-increasing circles: Seven-membered-ring ketones are constructed by a rhodium(I)-catalyzed arylative ring-expansion reaction of alkyne-substituted aryl cyclobutanones, in which two C-C bond-forming and one C-C bond-cleaving events occur consecutively (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4608 / 4611
页数:4
相关论文
共 29 条
[1]
Palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides to indanones and 2-cyclopentenones
Gagnier, SV
论文数:
0
引用数:
0
h-index:
0
机构:
Iowa State Univ, Dept Chem, Ames, IA 50010 USA
Iowa State Univ, Dept Chem, Ames, IA 50010 USA
Gagnier, SV
Larock, RC
论文数:
0
引用数:
0
h-index:
0
机构:
Iowa State Univ, Dept Chem, Ames, IA 50010 USA
Iowa State Univ, Dept Chem, Ames, IA 50010 USA
Larock, RC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(16)
: 4804
-
4807
[2]
Galli C, 2000, EUR J ORG CHEM, V2000, P3117
[3]
Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate
Hayashi, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Hayashi, T
Inoue, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Inoue, K
Taniguchi, N
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0
引用数:
0
h-index:
0
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Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Taniguchi, N
论文数:
引用数:
h-index:
机构:
Ogasawara, M
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(40)
: 9918
-
9919
[4]
RING-CLOSURE REACTIONS OF BIFUNCTIONAL CHAIN MOLECULES
ILLUMINATI, G
论文数:
0
引用数:
0
h-index:
0
ILLUMINATI, G
MANDOLINI, L
论文数:
0
引用数:
0
h-index:
0
MANDOLINI, L
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
1981,
14
(04)
: 95
-
102
[5]
Direct observation of aldehyde insertion into rhodium-aryl and -alkoxide complexes
Krug, C
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Krug, C
Hartwig, JF
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Hartwig, JF
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(08)
: 1674
-
1679
[6]
Rhodium-catalyzed tandem cyclization:: Formation of 1H-indenes and 1-alkylideneindans from arylboronate esters in aqueous media
Lautens, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada
Lautens, M
Marquardt, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada
Marquardt, T
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2004,
69
(14)
: 4607
-
4614
[7]
Regioselective rhodium-catalyzed addition of arylboronic acids to alkynes with a pyridine-substituted water-soluble ligand
Lautens, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
Lautens, M
Yoshida, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
Yoshida, M
[J].
ORGANIC LETTERS,
2002,
4
(01)
: 123
-
125
[8]
Rhodium-catalyzed addition/ring-opening reaction of arylboronic acids with cyclobutanones
Matsuda, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Matsuda, T
Makino, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Makino, M
Murakami, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Murakami, M
[J].
ORGANIC LETTERS,
2004,
6
(08)
: 1257
-
1259
[9]
MATSUDA T, 2005, IN PRESS B CHEM SOC
[10]
Progress in the construction of cyclooctanoid systems: New approaches and applications to natural product syntheses
Mehta, G
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
Mehta, G
Singh, V
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
Singh, V
[J].
CHEMICAL REVIEWS,
1999,
99
(03)
: 881
-
930
←
1
2
3
→
共 29 条
[1]
Palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides to indanones and 2-cyclopentenones
Gagnier, SV
论文数:
0
引用数:
0
h-index:
0
机构:
Iowa State Univ, Dept Chem, Ames, IA 50010 USA
Iowa State Univ, Dept Chem, Ames, IA 50010 USA
Gagnier, SV
Larock, RC
论文数:
0
引用数:
0
h-index:
0
机构:
Iowa State Univ, Dept Chem, Ames, IA 50010 USA
Iowa State Univ, Dept Chem, Ames, IA 50010 USA
Larock, RC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(16)
: 4804
-
4807
[2]
Galli C, 2000, EUR J ORG CHEM, V2000, P3117
[3]
Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate
Hayashi, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Hayashi, T
Inoue, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Inoue, K
Taniguchi, N
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
Taniguchi, N
论文数:
引用数:
h-index:
机构:
Ogasawara, M
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(40)
: 9918
-
9919
[4]
RING-CLOSURE REACTIONS OF BIFUNCTIONAL CHAIN MOLECULES
ILLUMINATI, G
论文数:
0
引用数:
0
h-index:
0
ILLUMINATI, G
MANDOLINI, L
论文数:
0
引用数:
0
h-index:
0
MANDOLINI, L
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
1981,
14
(04)
: 95
-
102
[5]
Direct observation of aldehyde insertion into rhodium-aryl and -alkoxide complexes
Krug, C
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Krug, C
Hartwig, JF
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Hartwig, JF
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(08)
: 1674
-
1679
[6]
Rhodium-catalyzed tandem cyclization:: Formation of 1H-indenes and 1-alkylideneindans from arylboronate esters in aqueous media
Lautens, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada
Lautens, M
Marquardt, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada
Marquardt, T
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2004,
69
(14)
: 4607
-
4614
[7]
Regioselective rhodium-catalyzed addition of arylboronic acids to alkynes with a pyridine-substituted water-soluble ligand
Lautens, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
Lautens, M
Yoshida, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
Yoshida, M
[J].
ORGANIC LETTERS,
2002,
4
(01)
: 123
-
125
[8]
Rhodium-catalyzed addition/ring-opening reaction of arylboronic acids with cyclobutanones
Matsuda, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Matsuda, T
Makino, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Makino, M
Murakami, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
Murakami, M
[J].
ORGANIC LETTERS,
2004,
6
(08)
: 1257
-
1259
[9]
MATSUDA T, 2005, IN PRESS B CHEM SOC
[10]
Progress in the construction of cyclooctanoid systems: New approaches and applications to natural product syntheses
Mehta, G
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
Mehta, G
Singh, V
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
Singh, V
[J].
CHEMICAL REVIEWS,
1999,
99
(03)
: 881
-
930
←
1
2
3
→