1,3-炔的化学、区域和立体选择性顺式硼氢化反应：铜催化获得 (Z,Z)- 和 (Z,E)-2-Boryl-1,3 二烯

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-07-17 DOI:10.1021/acs.orglett.4c0192910.1021/acs.orglett.4c01929

Nicklas W. Buchbinder, Long H. Nguyen, Owen N. Beck, Andrew D. Bage, Carla Slebodnick and Webster L. Santos*,

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引用次数: 0

摘要

本研究揭示了铜催化的 1,3-炔烃选择性氢硼化反应，从而获得了以前难以获得的 2-硼基-1,3-二烯。利用 CuOAc、Xantphos 和 HBpin，Bpin 被安装在一系列对称和非对称 1,3-烯炔的内部碳上，得到 Z:E 选择性极佳的产物。通过转化为有用的官能团，证明了 2-硼基-1,3-二烯产品的用途。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Chemo-, Regio-, and Stereoselective cis-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (Z,Z)- and (Z,E)-2-Boryl-1,3-dienes

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Chemo-, Regio-, and Stereoselective cis-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (Z,Z)- and (Z,E)-2-Boryl-1,3-dienes

A copper-catalyzed alkyne-selective hydroboration of 1,3-enynes is disclosed, providing access to the previously elusive 2-boryl-1,3-dienes. Using CuOAc, Xantphos, and HBpin, Bpin was installed on the internal carbon of a series of symmetric and nonsymmetric 1,3-enynes, affording products with excellent Z:E selectivity. The utility of the 2-boryl-1,3-diene products was demonstrated by transformation to useful functional groups.

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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.