Chelation versus Non-Chelation Control in the Stereoselective Alkenyl sp2 C−H Bond Functionalization Reaction

Qiu Ju Liang; Chao Yang; Fei Fan Meng; Bing Jiang; Yun He Xu; Teck Peng Loh

doi:10.1002/anie.201700559

Chelation versus Non-Chelation Control in the Stereoselective Alkenyl sp² C−H Bond Functionalization Reaction

Qiu Ju Liang, Chao Yang, Fei Fan Meng, Bing Jiang, Yun He Xu, Teck Peng Loh

School of Chemistry and Moleculai Engineering

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

73 Scopus citations

Abstract

A hydroxy group chelation-assisted stereospecific oxidative cross-coupling reaction between alkenes was developed under mild reaction conditions. In the presence of palladium catalyst, the alkenes tethered with hydroxy functionality can couple efficiently with electron-deficient alkenes to form the corresponding multi-substituted olefin products. The hydroxy group on the substrate could play dual roles in reaction, acting as the directing group for alkenyl C−H bond activation and controlling the stereoselectivity of the products.

Original language	English
Pages (from-to)	5091-5095
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	18
DOIs	https://doi.org/10.1002/anie.201700559
State	Published - 24 Apr 2017

Keywords

C−H activation
alkenylation
cross-coupling
palladium

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10.1002/anie.201700559

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title = "Chelation versus Non-Chelation Control in the Stereoselective Alkenyl sp2 C−H Bond Functionalization Reaction",

abstract = "A hydroxy group chelation-assisted stereospecific oxidative cross-coupling reaction between alkenes was developed under mild reaction conditions. In the presence of palladium catalyst, the alkenes tethered with hydroxy functionality can couple efficiently with electron-deficient alkenes to form the corresponding multi-substituted olefin products. The hydroxy group on the substrate could play dual roles in reaction, acting as the directing group for alkenyl C−H bond activation and controlling the stereoselectivity of the products.",

keywords = "C−H activation, alkenylation, cross-coupling, palladium",

author = "Liang, {Qiu Ju} and Chao Yang and Meng, {Fei Fan} and Bing Jiang and Xu, {Yun He} and Loh, {Teck Peng}",

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T1 - Chelation versus Non-Chelation Control in the Stereoselective Alkenyl sp2 C−H Bond Functionalization Reaction

AU - Liang, Qiu Ju

AU - Yang, Chao

AU - Meng, Fei Fan

AU - Jiang, Bing

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2017/4/24

Y1 - 2017/4/24

N2 - A hydroxy group chelation-assisted stereospecific oxidative cross-coupling reaction between alkenes was developed under mild reaction conditions. In the presence of palladium catalyst, the alkenes tethered with hydroxy functionality can couple efficiently with electron-deficient alkenes to form the corresponding multi-substituted olefin products. The hydroxy group on the substrate could play dual roles in reaction, acting as the directing group for alkenyl C−H bond activation and controlling the stereoselectivity of the products.

AB - A hydroxy group chelation-assisted stereospecific oxidative cross-coupling reaction between alkenes was developed under mild reaction conditions. In the presence of palladium catalyst, the alkenes tethered with hydroxy functionality can couple efficiently with electron-deficient alkenes to form the corresponding multi-substituted olefin products. The hydroxy group on the substrate could play dual roles in reaction, acting as the directing group for alkenyl C−H bond activation and controlling the stereoselectivity of the products.

KW - C−H activation

KW - alkenylation

KW - cross-coupling

KW - palladium

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U2 - 10.1002/anie.201700559

DO - 10.1002/anie.201700559

M3 - 文章

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AN - SCOPUS:85016805197

SN - 1433-7851

VL - 56

SP - 5091

EP - 5095

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 18

ER -

Chelation versus Non-Chelation Control in the Stereoselective Alkenyl sp² C−H Bond Functionalization Reaction

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Keywords

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