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

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.

SUBMITTER: Wang B

PROVIDER: S-EPMC8159320 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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

Wang Bin B Ong Derek Yiren DY Li Yihang Y Pang Jia Hao JH Watanabe Kohei K Takita Ryo R Chiba Shunsuke S

Chemical science 20200504 20

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 a ...[more]

PMID: 34122983

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