Generation of Allylmagnesium Reagents by Hydromagnesiation of 2-Aryl-1,3-dienes

Yihang Li; Jiahua Chen; Jaslyn Jing Wen Ng; Shunsuke Chiba

doi:10.1002/anie.202217735

Generation of Allylmagnesium Reagents by Hydromagnesiation of 2-Aryl-1,3-dienes

Yihang Li, Jiahua Chen, Jaslyn Jing Wen Ng, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

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

5 Citations (Scopus)

Abstract

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.

Original language	English
Article number	e202217735
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	10
DOIs	https://doi.org/10.1002/anie.202217735
Publication status	Published - Mar 1 2023
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

1,3-Dienes
Hydromagnesiation
Magnesium Hydride
Sodium Hydride

Access to Document

10.1002/anie.202217735

Cite this

@article{213ac7eb981a46de9af1496f398dc1f0,

title = "Generation of Allylmagnesium Reagents by Hydromagnesiation of 2-Aryl-1,3-dienes",

abstract = "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.",

keywords = "1,3-Dienes, Hydromagnesiation, Magnesium Hydride, Sodium Hydride",

author = "Yihang Li and Jiahua Chen and Ng, {Jaslyn Jing Wen} and Shunsuke Chiba",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = mar,

day = "1",

doi = "10.1002/anie.202217735",

language = "English",

volume = "62",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "10",

}

TY - JOUR

T1 - Generation of Allylmagnesium Reagents by Hydromagnesiation of 2-Aryl-1,3-dienes

AU - Li, Yihang

AU - Chen, Jiahua

AU - Ng, Jaslyn Jing Wen

AU - Chiba, Shunsuke

PY - 2023/3/1

Y1 - 2023/3/1

N2 - 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.

AB - 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.

KW - 1,3-Dienes

KW - Hydromagnesiation

KW - Magnesium Hydride

KW - Sodium Hydride

UR - http://www.scopus.com/inward/record.url?scp=85146762671&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85146762671&partnerID=8YFLogxK

U2 - 10.1002/anie.202217735

DO - 10.1002/anie.202217735

M3 - Article

C2 - 36637448

AN - SCOPUS:85146762671

SN - 1433-7851

VL - 62

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 10

M1 - e202217735

ER -

Generation of Allylmagnesium Reagents by Hydromagnesiation of 2-Aryl-1,3-dienes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

Other files and links

Fingerprint

Cite this