Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride

Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride

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 tetrahydro...

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Main Authors: Li, Yihang, Ng, Jia Sheng, Wang, Bin, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Functionalization
Redox Reactions
Online Access:https://hdl.handle.net/10356/154828
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1548282023-02-28T19:59:04Z Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride Li, Yihang Ng, Jia Sheng Wang, Bin Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Functionalization Redox Reactions 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. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by funding from Nanyang Technological University (NTU) and the Singapore Ministry of Education (Academic Research Fund Tier 2, MOE2019-T2-1-089). 2022-01-12T07:56:27Z 2022-01-12T07:56:27Z 2021 Journal Article Li, Y., Ng, J. S., Wang, B. & Chiba, S. (2021). Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride. Organic Letters, 23(13), 5060-5064. https://dx.doi.org/10.1021/acs.orglett.1c01583 1523-7060 https://hdl.handle.net/10356/154828 10.1021/acs.orglett.1c01583 34125560 2-s2.0-85108603035 13 23 5060 5064 en MOE2019-T2-1-089 Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.1c01583. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Functionalization
Redox Reactions
spellingShingle Science::Chemistry
Functionalization
Redox Reactions
Li, Yihang
Ng, Jia Sheng
Wang, Bin
Chiba, Shunsuke
Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Li, Yihang
Ng, Jia Sheng
Wang, Bin
Chiba, Shunsuke
format Article
author Li, Yihang
Ng, Jia Sheng
Wang, Bin
Chiba, Shunsuke
author_sort Li, Yihang
title Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride
title_short Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride
title_full Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride
title_fullStr Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride
title_full_unstemmed Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride
title_sort synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes with magnesium hydride
publishDate 2022
url https://hdl.handle.net/10356/154828
_version_ 1759855412934344704

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