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A new ruthenium-catalyzed hydrogen-transfer reaction: Transformation of 3-benzyl but-1-ynyl ethers into 1,3-dienes and benzaldehyde
被引:51
作者
:
Yeh, KL
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
Yeh, KL
[
1
]
Liu, B
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
Liu, B
[
1
]
Lo, CY
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
Lo, CY
[
1
]
论文数:
引用数:
h-index:
机构:
Huang, HL
[
1
]
Liu, RS
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
Liu, RS
[
1
]
机构
:
[1]
Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2002年
/ 124卷
/ 23期
关键词
:
D O I
:
10.1021/ja012623y
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equqtion Presentation) We report a ruthenium-catalyzed reaction for various 3-benzyl but-1-ynyl ethers with suitable functionalities. Treatment of these substrates with TpRu(PPh3)(CH3CN)2PF6 (8.0 mol %) catalyst in 1,2-dichloroethane (80 °C, 12 h) afforded functionalized 1,3-dienes and benzyl aldehyde in good yields. This process is considered to be a tandem dealkoxylation and transfer hydrogenation. Deuterium-labeling experiments reveal that the migration of different hydrogen atoms proceeds regiospecifically. A plausible mechanism is proposed on the basis of the results of isotope experiment. Copyright © 2002 American Chemical Society.
引用
收藏
页码:6510 / 6511
页数:2
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Department of Chemistry, Harvard University, Cambridge
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NELSON, SG
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Department of Chemistry, Harvard University, Cambridge
NELSON, SG
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GAGNE, MR
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Department of Chemistry, Harvard University, Cambridge
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Department of Chemistry, Harvard University, Cambridge
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ZACHARIAS, DM
.
ORGANOMETALLICS,
1993,
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←
1
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3
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→
共 34 条
[1]
Transition metal complexes containing allenylidene, cumulenylidene, and related ligands
[J].
Bruce, MI
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
Bruce, MI
.
CHEMICAL REVIEWS,
1998,
98
(08)
:2797
-2858
[2]
Metal vinylidenes in catalysis
[J].
Bruneau, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rennes, CNRS, UMR 6509, Lab Chim Coordinat & Catalyse, F-35042 Rennes, France
Univ Rennes, CNRS, UMR 6509, Lab Chim Coordinat & Catalyse, F-35042 Rennes, France
Bruneau, C
;
Dixneuf, PH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rennes, CNRS, UMR 6509, Lab Chim Coordinat & Catalyse, F-35042 Rennes, France
Univ Rennes, CNRS, UMR 6509, Lab Chim Coordinat & Catalyse, F-35042 Rennes, France
Dixneuf, PH
.
ACCOUNTS OF CHEMICAL RESEARCH,
1999,
32
(04)
:311
-323
[3]
Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes
[J].
Campbell, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
Campbell, EJ
;
Zhou, HY
论文数:
0
引用数:
0
h-index:
0
机构:
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
Zhou, HY
;
Nguyen, ST
论文数:
0
引用数:
0
h-index:
0
机构:
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
Nguyen, ST
.
ORGANIC LETTERS,
2001,
3
(15)
:2391
-2393
[4]
Syntheses and characterization of hydrotris(1-pyrazolyl)borate dihydrogen complexes of ruthenium and their roles in catalytic hydrogenation reactions
[J].
Chan, WC
论文数:
0
引用数:
0
h-index:
0
机构:
HONG KONG POLYTECH UNIV, DEPT APPL BIOL & CHEM TECHNOL, KOWLOON, HONG KONG
Chan, WC
;
Lau, CP
论文数:
0
引用数:
0
h-index:
0
机构:
HONG KONG POLYTECH UNIV, DEPT APPL BIOL & CHEM TECHNOL, KOWLOON, HONG KONG
Lau, CP
;
Chen, YZ
论文数:
0
引用数:
0
h-index:
0
机构:
HONG KONG POLYTECH UNIV, DEPT APPL BIOL & CHEM TECHNOL, KOWLOON, HONG KONG
Chen, YZ
;
Fang, YQ
论文数:
0
引用数:
0
h-index:
0
机构:
HONG KONG POLYTECH UNIV, DEPT APPL BIOL & CHEM TECHNOL, KOWLOON, HONG KONG
Fang, YQ
;
Ng, SM
论文数:
0
引用数:
0
h-index:
0
机构:
HONG KONG POLYTECH UNIV, DEPT APPL BIOL & CHEM TECHNOL, KOWLOON, HONG KONG
Ng, SM
;
Jia, GC
论文数:
0
引用数:
0
h-index:
0
机构:
HONG KONG POLYTECH UNIV, DEPT APPL BIOL & CHEM TECHNOL, KOWLOON, HONG KONG
Jia, GC
.
ORGANOMETALLICS,
1997,
16
(01)
:34
-44
[5]
A CHIRAL SAMARIUM-BASED CATALYST FOR THE ASYMMETRIC MEERWEIN-PONNDORF-VERLEY REDUCTION
[J].
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge
EVANS, DA
;
NELSON, SG
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge
NELSON, SG
;
GAGNE, MR
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge
GAGNE, MR
;
MUCI, AR
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge
MUCI, AR
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1993,
115
(21)
:9800
-9801
[6]
ASYMMETRIC CATALYTIC REDUCTION OF CARBONYL-COMPOUNDS USING C-2 SYMMETRICAL DIAMINES AS CHIRAL LIGANDS
[J].
GAMEZ, P
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV LYON 1,ESCIL,INST RECH CATALYSE,F-69622 VILLEURBANNE,FRANCE
GAMEZ, P
;
FACHE, F
论文数:
0
引用数:
0
h-index:
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机构:
UNIV LYON 1,ESCIL,INST RECH CATALYSE,F-69622 VILLEURBANNE,FRANCE
FACHE, F
;
LEMAIRE, M
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV LYON 1,ESCIL,INST RECH CATALYSE,F-69622 VILLEURBANNE,FRANCE
LEMAIRE, M
.
TETRAHEDRON-ASYMMETRY,
1995,
6
(03)
:705
-718
[7]
Ruthenium tris(pyrazolyl)borate complexes .1. Synthesis and reactivity of Ru(HB(pz)(3))(COD)X (X=Cl, Br) and Ru(HB(pz)(3))(L(2))Cl (L=nitrogen and phosphorus donor ligands)
[J].
Gemel, C
论文数:
0
引用数:
0
h-index:
0
机构:
VIENNA TECH UNIV,INST ORGAN CHEM,A-1060 VIENNA,AUSTRIA
Gemel, C
;
Trimmel, G
论文数:
0
引用数:
0
h-index:
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机构:
VIENNA TECH UNIV,INST ORGAN CHEM,A-1060 VIENNA,AUSTRIA
Trimmel, G
;
Slugovc, C
论文数:
0
引用数:
0
h-index:
0
机构:
VIENNA TECH UNIV,INST ORGAN CHEM,A-1060 VIENNA,AUSTRIA
Slugovc, C
;
Kremel, S
论文数:
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引用数:
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h-index:
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机构:
VIENNA TECH UNIV,INST ORGAN CHEM,A-1060 VIENNA,AUSTRIA
Kremel, S
;
Mereiter, K
论文数:
0
引用数:
0
h-index:
0
机构:
VIENNA TECH UNIV,INST ORGAN CHEM,A-1060 VIENNA,AUSTRIA
Mereiter, K
;
Schmid, R
论文数:
0
引用数:
0
h-index:
0
机构:
VIENNA TECH UNIV,INST ORGAN CHEM,A-1060 VIENNA,AUSTRIA
Schmid, R
;
Kirchner, K
论文数:
0
引用数:
0
h-index:
0
机构:
VIENNA TECH UNIV,INST ORGAN CHEM,A-1060 VIENNA,AUSTRIA
Kirchner, K
.
ORGANOMETALLICS,
1996,
15
(19)
:3998
-4004
[8]
GENET JP, 1993, SYNLETT, P478
[9]
GILLES B, 1995, B SOC CHIM FR, V132, P371
[10]
CATALYTIC TRANSFER HYDROGENATION OF BENZALDEHYDE IN A MICROWAVE-OVEN
[J].
GORDON, EM
论文数:
0
引用数:
0
h-index:
0
机构:
BALDWIN WALLACE COLL,DEPT CHEM,BEREA,OH 44017
BALDWIN WALLACE COLL,DEPT CHEM,BEREA,OH 44017
GORDON, EM
;
GABA, DC
论文数:
0
引用数:
0
h-index:
0
机构:
BALDWIN WALLACE COLL,DEPT CHEM,BEREA,OH 44017
BALDWIN WALLACE COLL,DEPT CHEM,BEREA,OH 44017
GABA, DC
;
JEBBER, KA
论文数:
0
引用数:
0
h-index:
0
机构:
BALDWIN WALLACE COLL,DEPT CHEM,BEREA,OH 44017
BALDWIN WALLACE COLL,DEPT CHEM,BEREA,OH 44017
JEBBER, KA
;
ZACHARIAS, DM
论文数:
0
引用数:
0
h-index:
0
机构:
BALDWIN WALLACE COLL,DEPT CHEM,BEREA,OH 44017
BALDWIN WALLACE COLL,DEPT CHEM,BEREA,OH 44017
ZACHARIAS, DM
.
ORGANOMETALLICS,
1993,
12
(12)
:5020
-5022
←
1
2
3
4
→