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芳基腈氧化物环加成反应在频哪醇硼酸酯存在下进行。

Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester.

机构信息

CSIRO Materials Science and Engineering, Private Bag 10, Clayton South MDC, Vic 3169, Australia.

出版信息

Beilstein J Org Chem. 2012;8:606-12. doi: 10.3762/bjoc.8.67. Epub 2012 Apr 19.

DOI:10.3762/bjoc.8.67
PMID:22563358
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3343286/
Abstract

An aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction.

摘要

一种具有双功能的芳基底物，由相应的醛肟经温和高价碘氧化（二醋酸碘苯）制备而成，其中硼酸酯官能团未分解。腈氧化物与各种偶极体就地捕获，生成硼酸酯功能完整且可用于后续反应的芳基异恶唑啉。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1fa5/3343286/b34040ec12c9/Beilstein_J_Org_Chem-08-606-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1fa5/3343286/a03b98043212/Beilstein_J_Org_Chem-08-606-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1fa5/3343286/3545e95912a0/Beilstein_J_Org_Chem-08-606-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1fa5/3343286/b34040ec12c9/Beilstein_J_Org_Chem-08-606-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1fa5/3343286/a03b98043212/Beilstein_J_Org_Chem-08-606-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1fa5/3343286/3545e95912a0/Beilstein_J_Org_Chem-08-606-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1fa5/3343286/b34040ec12c9/Beilstein_J_Org_Chem-08-606-g004.jpg

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本文引用的文献

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An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne.1,2-苯并异恶唑的改进合成：TBAF 介导的腈氧化物和苯炔的 1,3-偶极环加成反应。
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Modern synthetic methods for copper-mediated C(aryl)[bond]O, C(aryl)[bond]N, and C(aryl)[bond]S bond formation.用于铜介导的C（芳基）-O键、C（芳基）-N键和C（芳基）-S键形成的现代合成方法。
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