Palladium-Catalyzed Hiyama Cross-Coupling of Heterocyclic Phosphonium Salts with Arylsilanes

Ya Qi Liu; Rui Yang; Hongfang Li; Teck Peng Loh; Ming Zhu Lu

doi:10.1021/acs.orglett.5c00709

Palladium-Catalyzed Hiyama Cross-Coupling of Heterocyclic Phosphonium Salts with Arylsilanes

Ya Qi Liu, Rui Yang, Hongfang Li, Teck Peng Loh^*, Ming Zhu Lu^*

^*Corresponding author for this work

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

Abstract

We report herein the palladium-catalyzed Hiyama cross-coupling of heterocyclic phosphonium salts with diverse (hetero)arylsilanes through C-P bond cleavage, providing an alternative approach for the highly regioselective functionalization of pyridines and relevant nitrogen-containing heterocycles. This silicon-based protocol is amenable to gram-scale synthesis and also applicable to the late-stage functionalization of pharmaceutically relevant complex molecules.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.5c00709
Publication status	Accepted/In press - 2025
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "We report herein the palladium-catalyzed Hiyama cross-coupling of heterocyclic phosphonium salts with diverse (hetero)arylsilanes through C-P bond cleavage, providing an alternative approach for the highly regioselective functionalization of pyridines and relevant nitrogen-containing heterocycles. This silicon-based protocol is amenable to gram-scale synthesis and also applicable to the late-stage functionalization of pharmaceutically relevant complex molecules.",

author = "Liu, {Ya Qi} and Rui Yang and Hongfang Li and Loh, {Teck Peng} and Lu, {Ming Zhu}",

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year = "2025",

doi = "10.1021/acs.orglett.5c00709",

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

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AU - Liu, Ya Qi

AU - Yang, Rui

AU - Li, Hongfang

AU - Loh, Teck Peng

AU - Lu, Ming Zhu

PY - 2025

Y1 - 2025

N2 - We report herein the palladium-catalyzed Hiyama cross-coupling of heterocyclic phosphonium salts with diverse (hetero)arylsilanes through C-P bond cleavage, providing an alternative approach for the highly regioselective functionalization of pyridines and relevant nitrogen-containing heterocycles. This silicon-based protocol is amenable to gram-scale synthesis and also applicable to the late-stage functionalization of pharmaceutically relevant complex molecules.

AB - We report herein the palladium-catalyzed Hiyama cross-coupling of heterocyclic phosphonium salts with diverse (hetero)arylsilanes through C-P bond cleavage, providing an alternative approach for the highly regioselective functionalization of pyridines and relevant nitrogen-containing heterocycles. This silicon-based protocol is amenable to gram-scale synthesis and also applicable to the late-stage functionalization of pharmaceutically relevant complex molecules.

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JO - Organic Letters

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ER -

Palladium-Catalyzed Hiyama Cross-Coupling of Heterocyclic Phosphonium Salts with Arylsilanes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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