Palladium-catalyzed cross-coupling of unactivated alkenes with acrylates: Application to the synthesis of the C13-C21 fragment of palmerolide A

Zhen Kang Wen; Yun He Xu; Teck Peng Loh

doi:10.1002/chem.201201806

Palladium-catalyzed cross-coupling of unactivated alkenes with acrylates: Application to the synthesis of the C13-C21 fragment of palmerolide A

Zhen Kang Wen, Yun He Xu, Teck Peng Loh^*

^*Corresponding author for this work

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

47 Citations (Scopus)

Abstract

Diene to meet: A palladium-catalyzed cross-coupling reaction between alkyl-substituted olefins and acrylates gives the corresponding butadienes in moderate yield and stereoselectivity. This atom-economical reaction, which forms C sp 2-C sp 2 bonds, tolerates a wide range of allylic and homoallylic alcohols, and acrylates (see scheme; TIPS =triisopropylsilyl). The methodology was applied to the synthesis of the C13-C21 fragment of palmerolide A.

Original language	English
Pages (from-to)	13284-13287
Number of pages	4
Journal	Chemistry - A European Journal
Volume	18
Issue number	42
DOIs	https://doi.org/10.1002/chem.201201806
Publication status	Published - Oct 15 2012
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Organic Chemistry

Keywords

butadienes
C-H bond functionalization
cross-coupling
palladium
palmerolide A

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10.1002/chem.201201806

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title = "Palladium-catalyzed cross-coupling of unactivated alkenes with acrylates: Application to the synthesis of the C13-C21 fragment of palmerolide A",

abstract = "Diene to meet: A palladium-catalyzed cross-coupling reaction between alkyl-substituted olefins and acrylates gives the corresponding butadienes in moderate yield and stereoselectivity. This atom-economical reaction, which forms C sp 2-C sp 2 bonds, tolerates a wide range of allylic and homoallylic alcohols, and acrylates (see scheme; TIPS =triisopropylsilyl). The methodology was applied to the synthesis of the C13-C21 fragment of palmerolide A.",

keywords = "butadienes, C-H bond functionalization, cross-coupling, palladium, palmerolide A",

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T1 - Palladium-catalyzed cross-coupling of unactivated alkenes with acrylates

T2 - Application to the synthesis of the C13-C21 fragment of palmerolide A

AU - Wen, Zhen Kang

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2012/10/15

Y1 - 2012/10/15

N2 - Diene to meet: A palladium-catalyzed cross-coupling reaction between alkyl-substituted olefins and acrylates gives the corresponding butadienes in moderate yield and stereoselectivity. This atom-economical reaction, which forms C sp 2-C sp 2 bonds, tolerates a wide range of allylic and homoallylic alcohols, and acrylates (see scheme; TIPS =triisopropylsilyl). The methodology was applied to the synthesis of the C13-C21 fragment of palmerolide A.

AB - Diene to meet: A palladium-catalyzed cross-coupling reaction between alkyl-substituted olefins and acrylates gives the corresponding butadienes in moderate yield and stereoselectivity. This atom-economical reaction, which forms C sp 2-C sp 2 bonds, tolerates a wide range of allylic and homoallylic alcohols, and acrylates (see scheme; TIPS =triisopropylsilyl). The methodology was applied to the synthesis of the C13-C21 fragment of palmerolide A.

KW - butadienes

KW - C-H bond functionalization

KW - cross-coupling

KW - palladium

KW - palmerolide A

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JO - Chemistry - A European Journal

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Palladium-catalyzed cross-coupling of unactivated alkenes with acrylates: Application to the synthesis of the C13-C21 fragment of palmerolide A

Abstract

ASJC Scopus Subject Areas

Keywords

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