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LiCl-Mediated Preparation of Functionalized Benzylic Indium(III) Halides and Highly Chemoselective Palladium-Catalyzed Cross-Coupling in a Protic Cosolvent
被引:78
作者
:
Chen, Yi-Hung
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
Chen, Yi-Hung
[
1
]
Sun, Mai
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
Sun, Mai
[
1
]
Knochel, Paul
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
Knochel, Paul
[
1
]
机构
:
[1]
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2009年
/ 48卷
/ 12期
基金
:
欧洲研究理事会;
关键词
:
biaryls;
cross-coupling;
organoindium reagents;
palladium;
REAGENTS;
ARYL;
ORGANOMETALLICS;
COMPLEXES;
LIGANDS;
ACCESS;
ALLYL;
D O I
:
10.1002/anie.200805588
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) Sensitive functional groups such as COR, CHO, or CH2OH can be present in benzylic indium reagents prepared by the direct insertion of indium in the presence of LiCl. These reagents undergo palladium-catalyzed cross-coupling reactions in the presence of a protic cosolvent after activation with iPrMgCl·LiCl (see scheme). Remarkable chemoselectivities are achieved by using various electrophiles containing NH or OH groups. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2236 / 2239
页数:4
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Biaryl phosphane ligands in palladium-catalyzed amination
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Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
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[J].
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Trans-hydrometalation of alkynes by a combination of InCl3 and DIBAL-H:: One-pot access to functionalized (Z)-alkenes
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Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
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Palladium-catalyzed cross-coupling reaction of organoindiums with aryl halides in aqueous media
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Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
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1999
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A rationally designed universal catalyst for Suzuki-Miyaura coupling processes
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MIT, Dept Chem, Cambridge, MA 02139 USA
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Buchwald, SL
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2004,
43
(14)
: 1871
-
1876
[57]
WALKER SD, 2004, ANGEW CHEM, V116, P1907
[58]
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Efficient synthesis of symmetrically and unsymmetrically substituted hexaphenylbenzene analogues by Suzuki-Miyaura coupling reactions
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共 59 条
[51]
Biaryl phosphane ligands in palladium-catalyzed amination
Surry, David S.
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
Surry, David S.
Buchwald, Stephen L.
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, Stephen L.
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2008,
47
(34)
: 6338
-
6361
[52]
Suzuki A, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P123, DOI 10.1002/3527606548.ch3
[53]
Triethylborane-mediated hydrogallation and hydroindation: Novel access to organogalliums and organoindiums
Takami, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Takami, K
Mikami, S
论文数:
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引用数:
0
h-index:
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机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Mikami, S
Yorimitsu, H
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Yorimitsu, H
Shinokubo, H
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Shinokubo, H
Oshima, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Oshima, K
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(17)
: 6627
-
6631
[54]
Trans-hydrometalation of alkynes by a combination of InCl3 and DIBAL-H:: One-pot access to functionalized (Z)-alkenes
Takami, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Takami, K
Yorimitsu, H
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Yorimitsu, H
Oshima, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
Oshima, K
[J].
ORGANIC LETTERS,
2002,
4
(17)
: 2993
-
2995
[55]
Palladium-catalyzed cross-coupling reaction of organoindiums with aryl halides in aqueous media
Takami, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Takami, K
Yorimitsu, H
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Yorimitsu, H
Shinokubo, H
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Shinokubo, H
Matsubara, S
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Matsubara, S
Oshima, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
Oshima, K
[J].
ORGANIC LETTERS,
2001,
3
(13)
: 1997
-
1999
[56]
A rationally designed universal catalyst for Suzuki-Miyaura coupling processes
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
Walker, SD
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
Barder, TE
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
Martinelli, JR
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
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2004,
43
(14)
: 1871
-
1876
[57]
WALKER SD, 2004, ANGEW CHEM, V116, P1907
[58]
Wong C.-H., 2003, CARBOHYDRATE BASED D, VFirst
[59]
Efficient synthesis of symmetrically and unsymmetrically substituted hexaphenylbenzene analogues by Suzuki-Miyaura coupling reactions
Yang, Xiaoyin
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Polymer Res, D-55128 Mainz, Germany
Max Planck Inst Polymer Res, D-55128 Mainz, Germany
Yang, Xiaoyin
Don, Xi
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Polymer Res, D-55128 Mainz, Germany
Max Planck Inst Polymer Res, D-55128 Mainz, Germany
Don, Xi
Muellen, Klaus
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Polymer Res, D-55128 Mainz, Germany
Max Planck Inst Polymer Res, D-55128 Mainz, Germany
Muellen, Klaus
[J].
CHEMISTRY-AN ASIAN JOURNAL,
2008,
3
(04)
: 759
-
766
←
1
2
3
4
5
6
→