A synthesis of 1,3-dienes using a Ni(II) mediated Suzuki-Miyaura reaction

IF 1.3 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Bulletin of the Chemical Society of Ethiopia Pub Date : 2024-07-12 DOI:10.4314/bcse.v38i5.16

Yassir S. Al-Jawaheri, Nameer S. Ezzat

引用次数: 0

Abstract

Synthesis of the 1,3-dienes from arylboronic acids with propargyl alcohols using a Ni(II) precatalysts is presented. Through detailed reaction screening NiCl2(PCy3)2 has been identified as the optimal catalyst for this transformation. The reaction is thought to proceed through a Ni(II) allenyl complex, which undergoes a base free Suzuki-Miyaura cross-coupling through arylboronic acids, with the resultant aryl allene rearranging to its 1,3-diene. Application of these optimized reaction conditions then provides several dienes in reasonable to good, isolated yields. KEY WORDS: Suzuki-Miyaura, NiCl2(PCy3)2, 1,3-Dienes, Allenyl, Base free Bull. Chem. Soc. Ethiop. 2024, 38(5), 1405-1412. DOI: https://dx.doi.org/10.4314/bcse.v38i5.16

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利用 Ni(II) 介导的 Suzuki-Miyaura 反应合成 1,3-二烯

本文介绍了使用 Ni(II) 前催化剂从芳基硼酸与丙炔醇合成 1,3 二烯的过程。通过详细的反应筛选，NiCl2(PCy3)2 被确定为这种转化的最佳催化剂。该反应被认为是通过 Ni(II) 烯基络合物进行的，该络合物通过芳基硼酸进行无碱铃木-宫浦交叉偶联反应，由此产生的芳基烯烃重新排列为其 1,3-二烯。应用这些优化的反应条件，可以以合理到良好的分离产率获得多种二烯。关键词：Suzuki-Miyaura、NiCl2(PCy3)2、1,3-二烯、芳基、无碱 Bull.Chem.Soc.2024, 38(5), 1405-1412. DOI: https://dx.doi.org/10.4314/bcse.v38i5.16

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

Bulletin of the Chemical Society of Ethiopia 化学-化学综合

CiteScore

2.20

自引率

8.30%

发文量

113

审稿时长

6-12 weeks

期刊介绍： The Bulletin of the Chemical Society of Ethiopia (BCSE) is a triannual publication of the Chemical Society of Ethiopia. The BCSE is an open access and peer reviewed journal. The BCSE invites contributions in any field of basic and applied chemistry.