A Mild and General trans-Diboration of Both Terminal and Internal Propargyl Alcohols

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-28 DOI:10.1021/acs.orglett.4c03841

Yu-Tong Gu, Di-Di Chen, Cheng-Bin Wang, Qiushi Cheng, Jian-Rong Han, Xia Tian, Shouxin Liu, Wei Su

引用次数: 0

Abstract

A practical and efficient trans-diboration of propargyl alcohols was accomplished using sodium hydride (NaH) as a base in N,N-dimethylformamide at room temperature. The mild reaction conditions demonstrate general applicability, facilitating the successful conversion of both terminal and internal propargyl alcohols with diverse structures and functional groups into highly functionalized alkenediboronates [4-borylated 1,2-oxaborol-2(5H)-oles]. The resulting products, which incorporate two boron groups, can be selectively activated and subjected to stepwise transformations, thereby providing an effective platform for synthesizing a wide range of structurally diverse trisubstituted alkenes.

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温和而普遍的末端和内部丙炔醇反式二溴化反应

在室温下，以氢化钠（NaH）为碱，在 N,N-二甲基甲酰胺中完成了一种实用而高效的丙炔醇反式二丁化反应。温和的反应条件具有普遍的适用性，有助于将具有不同结构和官能团的末端和内部丙炔醇成功转化为高度官能化的烯化二硼酸盐[4-硼烷基化的 1,2-氧硼烷-2(5H)-醇]。所得产物含有两个硼基团，可选择性地活化并进行逐步转化，从而为合成各种结构不同的三取代烯提供了一个有效的平台。

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.