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

Haifeng Yu; Weiwei Jin; Chenglin Sun; Jiping Chen; Wangmin Du; Songbo He; Zhengkun Yu

doi:10.1002/anie.201002737

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

Haifeng Yu, Weiwei Jin, Chenglin Sun, Jiping Chen, Wangmin Du, Songbo He, Zhengkun Yu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

83 Citations (Scopus)

Abstract

A highly regioselective direct cross‐coupling of internal alkenes of α‐oxoketene dithioacetals with terminal alkenes has been successfully realized by palladium‐catalyzed CH bond activation, affording functionalized 1,3‐butadienes. Condensation of the resultant 1,3‐butadienes by diamines efficiently produced potentially bioactive bicyclic pyridone derivatives (see scheme).

Original language	English
Pages (from-to)	5792-5797
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	33
DOIs	https://doi.org/10.1002/anie.201002737
Publication status	Published - 2010
Externally published	Yes

Keywords

alkenes
alkenylation
C-H activation
heterocycles
palladium
PD(II)-CATALYZED OLEFINATION
DIRECT ALKENYLATION
DIRECT ARYLATION
DERIVATIVES
CYCLIZATION
REACTIVITY
COMPLEXES
ACRYLATES
LIBRARY
INDOLES

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@article{1d9d7d5f2c684470b29507a1204f9d05,

title = "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",

abstract = "A highly regioselective direct cross‐coupling of internal alkenes of α‐oxoketene dithioacetals with terminal alkenes has been successfully realized by palladium‐catalyzed CH bond activation, affording functionalized 1,3‐butadienes. Condensation of the resultant 1,3‐butadienes by diamines efficiently produced potentially bioactive bicyclic pyridone derivatives (see scheme).",

keywords = "alkenes, alkenylation, C-H activation, heterocycles, palladium, PD(II)-CATALYZED OLEFINATION, DIRECT ALKENYLATION, DIRECT ARYLATION, DERIVATIVES, CYCLIZATION, REACTIVITY, COMPLEXES, ACRYLATES, LIBRARY, INDOLES",

author = "Haifeng Yu and Weiwei Jin and Chenglin Sun and Jiping Chen and Wangmin Du and Songbo He and Zhengkun Yu",

year = "2010",

doi = "10.1002/anie.201002737",

language = "English",

volume = "49",

pages = "5792--5797",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "WILEY-V C H VERLAG GMBH",

number = "33",

}

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. / Yu, Haifeng; Jin, Weiwei; Sun, Chenglin et al.
In: Angewandte Chemie - International Edition, Vol. 49, No. 33, 2010, p. 5792-5797.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Palladium-Catalyzed Cross-Coupling of Internal Alkenes with Terminal Alkenes to Functionalized 1,3-Butadienes Using C-H Bond Activation

T2 - Efficient Synthesis of Bicyclic Pyridones

AU - Yu, Haifeng

AU - Jin, Weiwei

AU - Sun, Chenglin

AU - Chen, Jiping

AU - Du, Wangmin

AU - He, Songbo

AU - Yu, Zhengkun

PY - 2010

Y1 - 2010

N2 - A highly regioselective direct cross‐coupling of internal alkenes of α‐oxoketene dithioacetals with terminal alkenes has been successfully realized by palladium‐catalyzed CH bond activation, affording functionalized 1,3‐butadienes. Condensation of the resultant 1,3‐butadienes by diamines efficiently produced potentially bioactive bicyclic pyridone derivatives (see scheme).

AB - A highly regioselective direct cross‐coupling of internal alkenes of α‐oxoketene dithioacetals with terminal alkenes has been successfully realized by palladium‐catalyzed CH bond activation, affording functionalized 1,3‐butadienes. Condensation of the resultant 1,3‐butadienes by diamines efficiently produced potentially bioactive bicyclic pyridone derivatives (see scheme).

KW - alkenes

KW - alkenylation

KW - C-H activation

KW - heterocycles

KW - palladium

KW - PD(II)-CATALYZED OLEFINATION

KW - DIRECT ALKENYLATION

KW - DIRECT ARYLATION

KW - DERIVATIVES

KW - CYCLIZATION

KW - REACTIVITY

KW - COMPLEXES

KW - ACRYLATES

KW - LIBRARY

KW - INDOLES

U2 - 10.1002/anie.201002737

DO - 10.1002/anie.201002737

M3 - Article

SN - 1433-7851

VL - 49

SP - 5792

EP - 5797

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 33

ER -