Hydromagnesiation of 1,3-Enynes by Magnesium Hydride for Synthesis of Tri- and Tetra-substituted Allenes

Bin Wang; Yihang Li; Jia Hao Pang; Kohei Watanabe; Ryo Takita; Shunsuke Chiba

doi:10.1002/anie.202012027

Hydromagnesiation of 1,3-Enynes by Magnesium Hydride for Synthesis of Tri- and Tetra-substituted Allenes

Bin Wang, Yihang Li, Jia Hao Pang, Kohei Watanabe, Ryo Takita^*, Shunsuke Chiba^*

^*Corresponding author for this work

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

25 Citations (Scopus)

Abstract

A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI₂) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst.

Original language	English
Pages (from-to)	217-221
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	1
DOIs	https://doi.org/10.1002/anie.202012027
Publication status	Published - Jan 4 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

allenes
enynes
hydromagnesiation
magnesium hydride
sodium hydride

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10.1002/anie.202012027

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abstract = "A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst.",

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AU - Li, Yihang

AU - Pang, Jia Hao

AU - Watanabe, Kohei

AU - Takita, Ryo

AU - Chiba, Shunsuke

PY - 2021/1/4

Y1 - 2021/1/4

N2 - A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst.

AB - A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst.

KW - allenes

KW - enynes

KW - hydromagnesiation

KW - magnesium hydride

KW - sodium hydride

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ER -

Hydromagnesiation of 1,3-Enynes by Magnesium Hydride for Synthesis of Tri- and Tetra-substituted Allenes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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