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

^*Corresponding author for this work

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

73 Citations (Scopus)

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
Publication status	Published - Apr 24 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

alkenylation
cross-coupling
C−H activation
palladium

Access to Document

10.1002/anie.201700559

Cite this

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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.",

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AU - Yang, Chao

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AU - Jiang, Bing

AU - Xu, Yun He

AU - Loh, Teck Peng

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KW - cross-coupling

KW - C−H activation

KW - palladium

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