Generation of allylmagnesium reagents by hydromagnesiation of 2-Aryl-1,3-dienes

Generation of allylmagnesium reagents by hydromagnesiation of 2-Aryl-1,3-dienes

A protocol for the generation of allylmagnesium reagents from 2-aryl-1,3-dienes was developed using magnesium hydride (MgH2 ) that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2 ) in tetrahydrofuran (THF). Downstream functionalization of the resulti...

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Bibliographic Details
Main Authors: Li, Yihang, Chen, Jiahua, Ng, Jaslyn Jing Wen, Chiba, Shunsuke
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2023
Subjects:
Science::Chemistry
Hydromagnesiation
Sodium Hydride
Online Access:https://hdl.handle.net/10356/168875
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Institution: Nanyang Technological University
Language: English
Description
Summary:A protocol for the generation of allylmagnesium reagents from 2-aryl-1,3-dienes was developed using magnesium hydride (MgH2 ) that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2 ) in tetrahydrofuran (THF). Downstream functionalization of the resulting allylmagnesium reagents with carbonyl compounds or alkyl (pseudo)halides delivers branched products having an allylic quaternary carbon center, whereas that with chlorosilanes resulted in formation of linear allylsilanes in regio and stereoselective manners. Further derivatizations of the homoallylic alcohols and allylsilanes were also demonstrated.

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