Stereo-controlledanti-hydromagnesiation of aryl alkynes by magnesium hydrides

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

doi:10.1039/d0sc01773f

Stereo-controlledanti-hydromagnesiation of aryl alkynes by magnesium hydrides

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

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

A concise protocol foranti-hydromagnesiation of aryl alkynes was established using 1?:?1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI₂) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental and theoretical approaches imply that polar hydride addition from magnesium hydride (MgH₂) is responsible for the process.

Original language	English
Pages (from-to)	5267-5272
Number of pages	6
Journal	Chemical Science
Volume	11
Issue number	20
DOIs	https://doi.org/10.1039/d0sc01773f
Publication status	Published - May 28 2020
Externally published	Yes

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Publisher Copyright:
© The Royal Society of Chemistry 2020.

ASJC Scopus Subject Areas

General Chemistry

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abstract = "A concise protocol foranti-hydromagnesiation of aryl alkynes was established using 1?:?1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental and theoretical approaches imply that polar hydride addition from magnesium hydride (MgH2) is responsible for the process.",

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AU - Wang, Bin

AU - Ong, Derek Yiren

AU - Li, Yihang

AU - Pang, Jia Hao

AU - Watanabe, Kohei

AU - Takita, Ryo

AU - Chiba, Shunsuke

PY - 2020/5/28

Y1 - 2020/5/28

N2 - A concise protocol foranti-hydromagnesiation of aryl alkynes was established using 1?:?1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental and theoretical approaches imply that polar hydride addition from magnesium hydride (MgH2) is responsible for the process.

AB - A concise protocol foranti-hydromagnesiation of aryl alkynes was established using 1?:?1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental and theoretical approaches imply that polar hydride addition from magnesium hydride (MgH2) is responsible for the process.

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Stereo-controlledanti-hydromagnesiation of aryl alkynes by magnesium hydrides

Abstract

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