学术探索
学术期刊
新闻热点
数据分析
智能评审
立即登录
Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives
被引:107
作者
:
Johns, Adam M.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Johns, Adam M.
Liu, Zhijian
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Liu, Zhijian
Hartwig, John F.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Hartwig, John F.
机构
:
[1]
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
[2]
Yale Univ, Dept Chem, New Haven, CT 06520 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2007年
/ 46卷
/ 38期
关键词
:
allylic substitution;
homogeneous catalysis;
hydroamination;
palladium;
D O I
:
10.1002/anie.200701899
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) Amines of control: Palladium-catalyzed reactions of hydrazine and hydroxylamine derivatives with dienes and allylic esters form products from C-N bond formation at the more substituted position of the allyl intermediate with a broad range of ligands on palladium (see scheme; X=NCPh2 or OR; Ac = acetyl). These reactions provide a route to highly substituted primary amines by facile cleavage of the N-O and N-N bonds. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7259 / 7261
页数:3
相关论文
共 16 条
[1]
AMINATION OF PI-ALLYLPALLADIUM CHLORIDE COMPLEXES - A MECHANISTIC STUDY
[J].
AKERMARK, B
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
AKERMARK, B
;
AKERMARK, G
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
AKERMARK, G
;
HEGEDUS, LS
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
HEGEDUS, LS
;
ZETTERBERG, K
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
ZETTERBERG, K
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(11)
:3037
-3040
[2]
Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands
[J].
Atobe, M
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Atobe, M
;
Yamazaki, N
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Yamazaki, N
;
Kibayashi, C
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Kibayashi, C
.
JOURNAL OF ORGANIC CHEMISTRY,
2004,
69
(17)
:5595
-5607
[3]
Enantioselective allylation of ketone-derived benzoylhydrazones: Practical synthesis of tertiary carbinarnines
[J].
Berger, R
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
Berger, R
;
Duff, K
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
Duff, K
;
Leighton, JL
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
Leighton, JL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(18)
:5686
-5687
[4]
Regioselectivity in the palladium/(S)-BINAP(S)-catalyzed asymmetric allylic amination:: Reaction scope, kinetics, and stereodynamics
[J].
Faller, JW
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
Faller, JW
;
Wilt, JC
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
Wilt, JC
.
ORGANOMETALLICS,
2005,
24
(21)
:5076
-5083
[5]
Palladium/BINAP(S)-catalyzed asymmetric allylic amination
[J].
Faller, JW
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
Faller, JW
;
Wilt, JC
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
Wilt, JC
.
ORGANIC LETTERS,
2005,
7
(04)
:633
-636
[6]
Retention of regiochemistry of allylic esters in palladium-catalyzed allylic alkylation in the presence of a MOP ligand
[J].
Hayashi, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Hayashi, T
;
Kawatsura, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Kawatsura, M
;
Uozumi, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Uozumi, Y
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
(08)
:1681
-1687
[7]
A highly active palladium catalyst for intermolecular hydroamination. Factors that control reactivity and additions of functionalized anilines to dienes and vinylarenes
[J].
Johns, AM
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
Johns, AM
;
Utsunomiya, M
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
Utsunomiya, M
;
Incarvito, CD
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
Incarvito, CD
;
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
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(06)
:1828
-1839
[8]
KEIM W, 1983, J MOL CATAL, V20, P139, DOI 10.1016/0304-5102(83)83003-X
[9]
Palladium-catalyzed hydroamination of 1,3-dienes:: A colorimetric assay and enantioselective additions
[J].
Löber, O
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
Löber, O
;
Kawatsura, M
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
Kawatsura, M
;
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
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(18)
:4366
-4367
[10]
Utility of the iridium complex of the pybox ligand in regio- and enantioselective allylic substitution
[J].
Miyabe, H
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Miyabe, H
;
Matsumura, A
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Matsumura, A
;
Moriyama, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Moriyama, K
;
论文数:
引用数:
h-index:
机构:
Takemoto, Y
.
ORGANIC LETTERS,
2004,
6
(24)
:4631
-4634
←
1
2
→
共 16 条
[1]
AMINATION OF PI-ALLYLPALLADIUM CHLORIDE COMPLEXES - A MECHANISTIC STUDY
[J].
AKERMARK, B
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
AKERMARK, B
;
AKERMARK, G
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
AKERMARK, G
;
HEGEDUS, LS
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
HEGEDUS, LS
;
ZETTERBERG, K
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80521
ZETTERBERG, K
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(11)
:3037
-3040
[2]
Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands
[J].
Atobe, M
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Atobe, M
;
Yamazaki, N
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Yamazaki, N
;
Kibayashi, C
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
Kibayashi, C
.
JOURNAL OF ORGANIC CHEMISTRY,
2004,
69
(17)
:5595
-5607
[3]
Enantioselective allylation of ketone-derived benzoylhydrazones: Practical synthesis of tertiary carbinarnines
[J].
Berger, R
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
Berger, R
;
Duff, K
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
Duff, K
;
Leighton, JL
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
Leighton, JL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(18)
:5686
-5687
[4]
Regioselectivity in the palladium/(S)-BINAP(S)-catalyzed asymmetric allylic amination:: Reaction scope, kinetics, and stereodynamics
[J].
Faller, JW
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
Faller, JW
;
Wilt, JC
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
Wilt, JC
.
ORGANOMETALLICS,
2005,
24
(21)
:5076
-5083
[5]
Palladium/BINAP(S)-catalyzed asymmetric allylic amination
[J].
Faller, JW
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
Faller, JW
;
Wilt, JC
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
Wilt, JC
.
ORGANIC LETTERS,
2005,
7
(04)
:633
-636
[6]
Retention of regiochemistry of allylic esters in palladium-catalyzed allylic alkylation in the presence of a MOP ligand
[J].
Hayashi, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Hayashi, T
;
Kawatsura, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Kawatsura, M
;
Uozumi, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 60601, Japan
Uozumi, Y
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
(08)
:1681
-1687
[7]
A highly active palladium catalyst for intermolecular hydroamination. Factors that control reactivity and additions of functionalized anilines to dienes and vinylarenes
[J].
Johns, AM
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
Johns, AM
;
Utsunomiya, M
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
Utsunomiya, M
;
Incarvito, CD
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
Incarvito, CD
;
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
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(06)
:1828
-1839
[8]
KEIM W, 1983, J MOL CATAL, V20, P139, DOI 10.1016/0304-5102(83)83003-X
[9]
Palladium-catalyzed hydroamination of 1,3-dienes:: A colorimetric assay and enantioselective additions
[J].
Löber, O
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
Löber, O
;
Kawatsura, M
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
Kawatsura, M
;
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
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(18)
:4366
-4367
[10]
Utility of the iridium complex of the pybox ligand in regio- and enantioselective allylic substitution
[J].
Miyabe, H
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Miyabe, H
;
Matsumura, A
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Matsumura, A
;
Moriyama, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Moriyama, K
;
论文数:
引用数:
h-index:
机构:
Takemoto, Y
.
ORGANIC LETTERS,
2004,
6
(24)
:4631
-4634
←
1
2
→