Direct zincation of functionalized aromatics and heterocycles by using a magnesium base in the presence of ZnCl2

Zhibing Dong; Giuliano C. Clososki; Stefan H. Wunderlich; Andreas Unsinn; Jinshan Li; Paul Knochel

doi:10.1002/chem.200801558

Direct zincation of functionalized aromatics and heterocycles by using a magnesium base in the presence of ZnCl₂

Zhibing Dong, Giuliano C. Clososki, Stefan H. Wunderlich, Andreas Unsinn, Jinshan Li, Paul Knochel

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

81 Scopus citations

Abstract

A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF by using (TMP)₂:Mg·2LiCl (TMP = 2,2,6,6-tetramethylpiperamidyl) in the presence of ZnCl₂. The possible pathways of this metalation procedure as well as possible reactive intermediates are discussed. This experimental protocol expands the tolerance of functional groups and allows an efficient zincation of sensitive heterocycles such as quinoxaline or pyrazine. The zincated arenes and heteroarenes react with various electrophiles providing the expected products in 60-95 % yield.

Original language	English
Pages (from-to)	457-468
Number of pages	12
Journal	Chemistry - A European Journal
Volume	15
Issue number	2
DOIs	https://doi.org/10.1002/chem.200801558
State	Published - 2 Jan 2009
Externally published	Yes

Keywords

Cross-coupling
Heterocycles
Metalation
Organometallics
Zincation

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10.1002/chem.200801558

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abstract = "A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF by using (TMP)2:Mg·2LiCl (TMP = 2,2,6,6-tetramethylpiperamidyl) in the presence of ZnCl2. The possible pathways of this metalation procedure as well as possible reactive intermediates are discussed. This experimental protocol expands the tolerance of functional groups and allows an efficient zincation of sensitive heterocycles such as quinoxaline or pyrazine. The zincated arenes and heteroarenes react with various electrophiles providing the expected products in 60-95 % yield.",

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AU - Dong, Zhibing

AU - Clososki, Giuliano C.

AU - Wunderlich, Stefan H.

AU - Unsinn, Andreas

AU - Li, Jinshan

AU - Knochel, Paul

PY - 2009/1/2

Y1 - 2009/1/2

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AB - A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF by using (TMP)2:Mg·2LiCl (TMP = 2,2,6,6-tetramethylpiperamidyl) in the presence of ZnCl2. The possible pathways of this metalation procedure as well as possible reactive intermediates are discussed. This experimental protocol expands the tolerance of functional groups and allows an efficient zincation of sensitive heterocycles such as quinoxaline or pyrazine. The zincated arenes and heteroarenes react with various electrophiles providing the expected products in 60-95 % yield.

KW - Cross-coupling

KW - Heterocycles

KW - Metalation

KW - Organometallics

KW - Zincation

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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Direct zincation of functionalized aromatics and heterocycles by using a magnesium base in the presence of ZnCl₂

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Keywords

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