Synthesis of α-Alkynylnitrones via Hydromagnesiation of 1,3-Enynes with Magnesium Hydride

Yihang Li; Jia Sheng Ng; Bin Wang; Shunsuke Chiba

doi:10.1021/acs.orglett.1c01583

Synthesis of α-Alkynylnitrones via Hydromagnesiation of 1,3-Enynes with Magnesium Hydride

Yihang Li, Jia Sheng Ng, Bin Wang, Shunsuke Chiba

Nanyang Technological University

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

9 Citations (Scopus)

Abstract

A protocol for the synthesis of α-Alkynylnitrones from 1,3-enynes has been developed. The process is triggered by hydromagnesiation of 1,3-enynes with magnesium hydride (MgH2), which is prepared in situ through solvothermal treatment of magnesium iodide (MgI2) with sodium hydride (NaH) in tetrahydrofuran. Downstream functionalization of the resulting propargylmagnesium intermediates with organo nitro compounds affords α-Alkynylnitrones, which could be used as versatile precursors for the construction of various nitrogen-containing compounds.

Original language	English
Pages (from-to)	5060-5064
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.1c01583
Publication status	Published - Jul 2 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.1c01583

Cite this

@article{7a5aec76b15e4b0290279265ec6d7a0f,

title = "Synthesis of α-Alkynylnitrones via Hydromagnesiation of 1,3-Enynes with Magnesium Hydride",

abstract = "A protocol for the synthesis of α-Alkynylnitrones from 1,3-enynes has been developed. The process is triggered by hydromagnesiation of 1,3-enynes with magnesium hydride (MgH2), which is prepared in situ through solvothermal treatment of magnesium iodide (MgI2) with sodium hydride (NaH) in tetrahydrofuran. Downstream functionalization of the resulting propargylmagnesium intermediates with organo nitro compounds affords α-Alkynylnitrones, which could be used as versatile precursors for the construction of various nitrogen-containing compounds.",

author = "Yihang Li and Ng, {Jia Sheng} and Bin Wang and Shunsuke Chiba",

year = "2021",

month = jul,

day = "2",

doi = "10.1021/acs.orglett.1c01583",

language = "English",

volume = "23",

pages = "5060--5064",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Synthesis of α-Alkynylnitrones via Hydromagnesiation of 1,3-Enynes with Magnesium Hydride

AU - Li, Yihang

AU - Ng, Jia Sheng

AU - Wang, Bin

AU - Chiba, Shunsuke

PY - 2021/7/2

Y1 - 2021/7/2

N2 - A protocol for the synthesis of α-Alkynylnitrones from 1,3-enynes has been developed. The process is triggered by hydromagnesiation of 1,3-enynes with magnesium hydride (MgH2), which is prepared in situ through solvothermal treatment of magnesium iodide (MgI2) with sodium hydride (NaH) in tetrahydrofuran. Downstream functionalization of the resulting propargylmagnesium intermediates with organo nitro compounds affords α-Alkynylnitrones, which could be used as versatile precursors for the construction of various nitrogen-containing compounds.

AB - A protocol for the synthesis of α-Alkynylnitrones from 1,3-enynes has been developed. The process is triggered by hydromagnesiation of 1,3-enynes with magnesium hydride (MgH2), which is prepared in situ through solvothermal treatment of magnesium iodide (MgI2) with sodium hydride (NaH) in tetrahydrofuran. Downstream functionalization of the resulting propargylmagnesium intermediates with organo nitro compounds affords α-Alkynylnitrones, which could be used as versatile precursors for the construction of various nitrogen-containing compounds.

UR - http://www.scopus.com/inward/record.url?scp=85108603035&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85108603035&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c01583

DO - 10.1021/acs.orglett.1c01583

M3 - Article

C2 - 34125560

AN - SCOPUS:85108603035

SN - 1523-7060

VL - 23

SP - 5060

EP - 5064

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Synthesis of α-Alkynylnitrones via Hydromagnesiation of 1,3-Enynes with Magnesium Hydride

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this