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Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: An entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction
被引:185
作者
:
Nakao, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Nakao, Y
[
1
]
Imanaka, H
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Imanaka, H
[
1
]
Sahoo, AK
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Sahoo, AK
[
1
]
Yada, A
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Yada, A
[
1
]
Hiyama, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
Hiyama, T
[
1
]
机构
:
[1]
Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2005年
/ 127卷
/ 19期
关键词
:
D O I
:
10.1021/ja051281j
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3 as a base, significantly milder conditions compared with those ever reported for the silicon-based cross-coupling reactions. The reaction tolerates a wide range of functional groups, including silyl protectors, and allows a gram-scale synthesis to recover and reuse the silicon residue. Copyright © 2005 American Chemical Society.
引用
收藏
页码:6952 / 6953
页数:2
相关论文
共 36 条
[1]
Vinyldimethylphenylsilanes as safety catch silanols in fluoride-free palladium-catalyzed cross-coupling reactions
[J].
Anderson, JC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
Anderson, JC
;
Munday, RH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
Munday, RH
.
JOURNAL OF ORGANIC CHEMISTRY,
2004,
69
(25)
:8971
-8974
[2]
A CONVENIENT AND NOVEL ROUTE TO BIS(ETA-ALKYNE)PLATINUM(0) AND OTHER PLATINUM(0) COMPLEXES FROM SPEIER HYDROSILYLATION CATALYST H2[PTCL6].XH2O - X-RAY STRUCTURE OF [PT((ETA-CH2=CHSIME2)2O)(P-TERT-BU3)]
[J].
CHANDRA, G
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
CHANDRA, G
;
LO, PY
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
LO, PY
;
HITCHCOCK, PB
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
HITCHCOCK, PB
;
LAPPERT, MF
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
LAPPERT, MF
.
ORGANOMETALLICS,
1987,
6
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:191
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[3]
REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES
[J].
CHUIT, C
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
CHUIT, C
;
CORRIU, RJP
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
CORRIU, RJP
;
REYE, C
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
REYE, C
;
YOUNG, JC
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
YOUNG, JC
.
CHEMICAL REVIEWS,
1993,
93
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:1371
-1448
[4]
Denmark S.E., 2004, Metal-Catalyzed Cross-Coupling Reactions, V1, P163, DOI DOI 10.1002/9783527619535.CH4
[5]
Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
Denmark, SE
;
Ober, MH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
Ober, MH
.
ADVANCED SYNTHESIS & CATALYSIS,
2004,
346
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:1703
-1714
[6]
Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanois with substituted aryl halides
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Denmark, SE
;
Baird, JD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Baird, JD
.
ORGANIC LETTERS,
2004,
6
(20)
:3649
-3652
[7]
Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, SE
;
Sweis, RF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Sweis, RF
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
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:4876
-4882
[8]
Tandem intramolecular silylformylation and silicon-assisted cross-coupling reactions.: Synthesis of geometrically defined α,β-unsaturated aldehydes
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, SE
;
Kobayashi, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Kobayashi, T
.
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(13)
:5153
-5159
[9]
Fluoride-free cross-coupling of organosilanols
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Denmark, SE
;
Sweis, RF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Sweis, RF
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
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:6439
-6440
[10]
Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, SE
;
Choi, JY
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Choi, JY
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(24)
:5821
-5822
←
1
2
3
4
→
共 36 条
[1]
Vinyldimethylphenylsilanes as safety catch silanols in fluoride-free palladium-catalyzed cross-coupling reactions
[J].
Anderson, JC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
Anderson, JC
;
Munday, RH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
Munday, RH
.
JOURNAL OF ORGANIC CHEMISTRY,
2004,
69
(25)
:8971
-8974
[2]
A CONVENIENT AND NOVEL ROUTE TO BIS(ETA-ALKYNE)PLATINUM(0) AND OTHER PLATINUM(0) COMPLEXES FROM SPEIER HYDROSILYLATION CATALYST H2[PTCL6].XH2O - X-RAY STRUCTURE OF [PT((ETA-CH2=CHSIME2)2O)(P-TERT-BU3)]
[J].
CHANDRA, G
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
CHANDRA, G
;
LO, PY
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
LO, PY
;
HITCHCOCK, PB
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
HITCHCOCK, PB
;
LAPPERT, MF
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
LAPPERT, MF
.
ORGANOMETALLICS,
1987,
6
(01)
:191
-192
[3]
REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES
[J].
CHUIT, C
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
CHUIT, C
;
CORRIU, RJP
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
CORRIU, RJP
;
REYE, C
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
REYE, C
;
YOUNG, JC
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
UNIV MONTPELLIER 2,HETEROCHIM & AMINOACIDES LAB,CNRS,URA 1097,PL E BATAILLON,F-34060 MONTPELLIER,FRANCE
YOUNG, JC
.
CHEMICAL REVIEWS,
1993,
93
(04)
:1371
-1448
[4]
Denmark S.E., 2004, Metal-Catalyzed Cross-Coupling Reactions, V1, P163, DOI DOI 10.1002/9783527619535.CH4
[5]
Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
Denmark, SE
;
Ober, MH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
Ober, MH
.
ADVANCED SYNTHESIS & CATALYSIS,
2004,
346
(13-15)
:1703
-1714
[6]
Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanois with substituted aryl halides
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Denmark, SE
;
Baird, JD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Baird, JD
.
ORGANIC LETTERS,
2004,
6
(20)
:3649
-3652
[7]
Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, SE
;
Sweis, RF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Sweis, RF
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(15)
:4876
-4882
[8]
Tandem intramolecular silylformylation and silicon-assisted cross-coupling reactions.: Synthesis of geometrically defined α,β-unsaturated aldehydes
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, SE
;
Kobayashi, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Kobayashi, T
.
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(13)
:5153
-5159
[9]
Fluoride-free cross-coupling of organosilanols
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Denmark, SE
;
Sweis, RF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Sweis, RF
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(26)
:6439
-6440
[10]
Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes
[J].
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, SE
;
Choi, JY
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Choi, JY
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(24)
:5821
-5822
←
1
2
3
4
→