Solvent control of E/Z selectivity in palladium-catalyzed semi-hydrogenation of alkynes†

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-05-07 DOI:10.1039/d5ob00295h

Yuang Chen , Tianna Jing , Zhihua Cai , Qingqing Bu

引用次数: 0

Abstract

A solvent-controlled stereoselective semi-reduction of alkynes with excellent stereoselectivity and chemoselectivity was accomplished by palladium catalysis. Various Z-alkenes were achieved with formic acid as the hydrogen source when the reaction was conducted in DMSO, while E-alkenes were obtained in toluene under otherwise identical reaction conditions. Detailed mechanism studies suggested that the alkyne hydrogenation gave Z-alkene intermediates. The E-alkene product was generated by a Z to E alkene isomerization process in toluene, and the Z-alkene was stabilized by employing DMSO as the solvent.

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钯催化炔烃半加氢反应E/Z选择性的溶剂控制。

以钯为催化剂，实现了具有良好立体选择性和化学选择性的溶剂控制立体选择性半还原反应。在DMSO中以甲酸为氢源反应得到多种z -烯烃，在其他条件相同的情况下以甲苯为氢源反应得到e -烯烃。详细的机理研究表明，炔加氢生成了z -烯烃中间体。在甲苯中进行Z- E-烯烃异构化反应生成E-烯烃产物，采用DMSO作为溶剂对Z-烯烃进行稳定。

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 & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.