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 ^{[1
]}

Liu, B ^{[1
]}

Lo, CY ^{[1
]}

Huang, HL ^{[1
]}

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

页码：6510 / 6511

页数：2

共 34 条

[1] Ruthenium-catalyzed transformation of 3-benzyl but-1-ynyl ethers into 1,3-dienes and benzaldehyde via transfer hydrogen
Yeh, KL
Liu, B
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Li, CW
Liu, RS
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14): : 4692 - 4694
[2] Ruthenium-Catalyzed Synthesis of Functionalized 1,3-Dienes
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[3] A ruthenium-catalyzed two-component addition to form 1,3-dienes
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[4] NOVEL, INTRAMOLECULAR HYDROGEN-TRANSFER AND CYCLOADDITION PHOTOCHEMISTRY OF CYCLIC 1,3-DIENES
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KOOLE, LH
CLAESSENS, HA
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[5] Ruthenium-Catalyzed Multicomponent Reactions: Access to -Silyl--Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes
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[6] REACTION OF 3-SULFOLENE WITH 1,3-DIENES, CATALYZED BY PALLADIUM COMPLEXES
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[7] Ruthenium-catalyzed two-component addition to form 1,3-dienes: Optimization, scope, applications, and mechanism
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[8] The Ruthenium-Catalyzed Hydrovinylation of Internal Alkynes by Acrylates: An Atom Economic Approach to Highly Substituted 1,3-Dienes
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[9] Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (E,E)-1,3-Dienes
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JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (04): : 3444 - 3455
[10] SYNTHESIS OF SUBSTITUTED 1,3-DIENES BY THE REACTION OF ALKENESULFONYL CHLORIDES WITH OLEFINS CATALYZED BY A RUTHENIUM(II) COMPLEX
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SATOH, T
KAMIGATA, N
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (04) : 1231 - 1235

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