Palladium-Catalyzed Elimination/Isomerization of Enol Triflates into 1,3-Dienes

被引：45

作者：

Crouch, Ian T. ^{[1
]}

Dreier, Timothy ^{[1
]}

Frantz, Doug E. ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 27期

关键词：

dienes; enol triflates; homogeneous catalysis; palladium; synthetic methods; CROSS-COUPLING REACTION; STEREOSELECTIVE-SYNTHESIS; CONJUGATED DIENES; ISOMERIZATION; TOSYLATES; ALKENES; ESTERS; OLEFINATION; METATHESIS; PHOSPHATES;

D O I：

10.1002/anie.201101820

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dying to be Dienes: Substituted 1,3-dienes were synthesized by the title reaction (see scheme; Tf=trifluoromethanesulfonyl). Preliminary studies support a mechanistically distinct pathway that involves an initial β-hydride elimination from a cationic vinyl palladium(II) intermediate, a subsequent regiospecific hydropalladation of the corresponding allene intermediate, and a final β-hydride elimination. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6128 / 6132

页数：5

共 33 条

[31]

Yu H., 2010, ANGEW CHEM INT EDIT, V122, P5928

[32] Palladium-Catalyzed Cross-Coupling of Internal Alkenes with Terminal Alkenes to Functionalized 1,3-Butadienes Using C-H Bond Activation: Efficient Synthesis of Bicyclic Pyridones [J].

Yu, Haifeng ;

Jin, Weiwei ;

Sun, Chenglin ;

Chen, Jiping ;

Du, Wangmin ;

He, Songbo ;

Yu, Zhengkun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (33) :5792-5797

[33] Streamlined Syntheses of (-)-Dictyostatin, 16-Desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-Desmethyl-25,26-dihydrodictyostatin [J].

Zhu, Wei ;

Jimenez, Maria ;

Jung, Won-Hyuk ;

Camarco, Daniel P. ;

Balachandran, Raghavan ;

Vogt, Andreas ;

Day, Billy W. ;

Curran, Dennis P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) :9175-9187

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