A general strategy toward aromatic 1,2-ambiphilic synthons: Palladium-catalyzed ortho-halogenation of PyDipSi-arenes

Alexander S. Dudnik; Natalia Chernyak; Chunhui Huang; Vladimir Gevorgyan

doi:10.1002/anie.201004426

A general strategy toward aromatic 1,2-ambiphilic synthons: Palladium-catalyzed ortho-halogenation of PyDipSi-arenes

Alexander S. Dudnik, Natalia Chernyak, Chunhui Huang, Vladimir Gevorgyan

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

93 Scopus citations

Abstract

A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.

Original language	English (US)
Pages (from-to)	8729-8732
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	46
DOIs	https://doi.org/10.1002/anie.201004426
State	Published - Nov 8 2010
Externally published	Yes

Keywords

C-H activation
benzynes
halogenation
palladium
siloles

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201004426

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keywords = "C-H activation, benzynes, halogenation, palladium, siloles",

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AU - Dudnik, Alexander S.

AU - Chernyak, Natalia

AU - Huang, Chunhui

AU - Gevorgyan, Vladimir

PY - 2010/11/8

Y1 - 2010/11/8

N2 - A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.

AB - A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.

KW - C-H activation

KW - benzynes

KW - halogenation

KW - palladium

KW - siloles

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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IS - 46

ER -

A general strategy toward aromatic 1,2-ambiphilic synthons: Palladium-catalyzed ortho-halogenation of PyDipSi-arenes

Abstract

Keywords

ASJC Scopus subject areas

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