Dual 1,2-Migration-Enabled β-Boryl Amide Synthesis.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-11 Epub Date: 2025-07-02 DOI:10.1021/acs.orglett.5c02107

Qi Cheng, Hanlin Yang, Shunle Hu, Xingwei Li, Songjie Yu

引用次数: 0

Abstract

A metal-free approach for the synthesis of multisubstituted β-boryl amides is achieved via the couplings of dioxazolones with readily accessible vinyl boronate complexes. The dioxazolones undergo a Curtius-type rearrangement, in situ generating electrophilic isocyanates that subsequently react with vinyl boronate complexes. This mechanistically distinct approach enables the efficient construction of structurally diverse β-boryl amides featuring a borylated quaternary carbon center. The synthetic versatility of this protocol is further demonstrated through multiple downstream transformations of both the boron and carbonyl moieties.

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双1,2-迁移激活β-硼酰酰胺合成

通过二恶唑酮与易于获得的乙烯基硼酸配合物的偶联，实现了合成多取代β-硼酸酰胺的无金属方法。二恶唑酮经过curtius型重排，在原位生成亲电异氰酸酯，随后与乙烯基硼酸配合物反应。这种机制上独特的方法能够有效地构建具有硼化季碳中心的结构多样的β-硼酰酰胺。通过硼和羰基部分的多次下游转化，进一步证明了该方案的合成通用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.