Synthesis of 1,3-Dienes via a Sequential Suzuki–Miyaura Coupling/Palladium-Mediated Allene Isomerization Sequence,Organic Letters

当前位置： X-MOL 学术 › Org. Lett. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis of 1,3-Dienes via a Sequential Suzuki–Miyaura Coupling/Palladium-Mediated Allene Isomerization Sequence
Organic Letters ( IF 4.9 ) Pub Date : 2016-06-29 00:00:00 , DOI: 10.1021/acs.orglett.6b01841
Yassir Al-Jawaheri ₁ , Marc C. Kimber ₁

Affiliation

We report a facile method for the synthesis of 1,3-dienes by a sequential process consisting of a palladium-catalyzed, base-free, Suzuki–Miyaura coupling/isomerization sequence. This sequence couples boronic acids with propargyl alcohols, generating the requisite allene in situ, followed by conversion of the unactivated allene to its 1,3-diene via a hydro-palladation/dehydro-palladation process. This process is general for a range of boronic acids, including boronic acids with electron-donating and -withdrawing groups, as well as heteroarylboronic acids. Key to this process is the boric acid byproduct of the base-free Suzuki–Miyauru coupling, which generates the required palladium–hydrido complex [H–Pd^II–OB(OH)₂] required for the isomerization.

中文翻译：

通过顺序的Suzuki-Miyaura偶联/钯介导的异戊烯异构化序列合成1,3-二烯

我们报告了一种由钯催化，无碱，Suzuki-Miyaura偶联/异构化序列组成的顺序过程，用于合成1,3-二烯的简便方法。该序列将硼酸与炔丙醇偶合，在原位生成必需的丙二烯，然后通过加氢palpalation /脱氢palpalation过程将未活化的alene转化为其1,3-二烯。对于一系列硼酸，包括具有给电子和吸电子基团的硼酸，以及杂芳基硼酸，该方法是通用的。该过程的关键是无碱Suzuki-Miyauru偶联的硼酸副产物，该副产物可生成异构化所需的钯-氢络合物[H-Pd ^II -OB（OH）₂ ]。

更新日期：2016-06-29

点击分享查看原文

点击收藏

公开下载

阅读更多本刊新发论文本刊介绍/投稿指南