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Issue 20, 2020
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Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides

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Abstract

A concise protocol for anti-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.

Graphical abstract: Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides

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Supplementary files

Article information


Submitted
27 Mar 2020
Accepted
02 May 2020
First published
04 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 5267-5272
Article type
Edge Article

Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides

B. Wang, D. Y. Ong, Y. Li, J. H. Pang, K. Watanabe, R. Takita and S. Chiba, Chem. Sci., 2020, 11, 5267
DOI: 10.1039/D0SC01773F

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