Hypervalent Iodine Reagents Enable C–H Alkynylation with Iminophenylacetic Acids via Alkoxyl Radicals,Organic Letters

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Hypervalent Iodine Reagents Enable C–H Alkynylation with Iminophenylacetic Acids via Alkoxyl Radicals
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-05 , DOI: 10.1021/acs.orglett.2c02210
Zhengyi Liu ₁ , Yue Pan _{1,

2} , Peng Zou ₁ , Hanchu Huang ₁ , Yali Chen ₂ , Yiyun Chen _{1,

3,

4}

Affiliation

Here we report δ-C–H alkynylation to synthesize various δ-alkynols from iminophenylacetic acids. The hypervalent iodine-coordinated benziodoxole-alkoxyl-iminophenylacetic acid complex was the key intermediate and was characterized by X-ray crystallography for the first time. δ-C–H alkynylation is compatible with sensitive functional groups, including azides, aldehydes, and free alcohols, for the synthesis of δ-alkynols with diversified substituents in excellent regioselectivity. This reaction extends to δ-hydroxylalkene and δ-hydroxylnitrile synthesis, and the δ-alkynol products are easily derivatized to other valuable bifunctional building blocks.

中文翻译：

高价碘试剂通过烷氧基自由基与亚氨基苯乙酸实现 C-H 炔基化

在这里，我们报告了 δ-C-H 炔基化以从亚氨基苯乙酸合成各种 δ-炔醇。高价碘配位的苯并氧唑-烷氧基-亚氨基苯乙酸络合物是关键中间体，首次通过X射线晶体学对其进行了表征。δ-C-H 炔基化与敏感官能团相容，包括叠氮化物、醛和游离醇，用于合成具有优异区域选择性的多种取代基的 δ-炔醇。该反应扩展到 δ-羟基烯烃和 δ-羟基腈的合成，δ-炔醇产物很容易衍生为其他有价值的双功能结构单元。

更新日期：2022-08-05

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