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

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81 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	457-468
页数	12
期刊	Chemistry - A European Journal
卷	15
期	2
DOI	https://doi.org/10.1002/chem.200801558
出版状态	已出版 - 2 1月 2009
已对外发布	是

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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

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N2 - 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.

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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SN - 0947-6539

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