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钯催化的Suzuki-Miyaura偶联反应不对称构建芳基-烯烃轴
作者:小柯机器人 发布时间:2022/9/21 14:41:05

南方科技大学谭斌团队报道了钯催化的Suzuki-Miyaura偶联反应不对称构建芳基-烯烃轴。相关研究成果于2022年9月16日发表在《德国应用化学》。

Suzuki-Miyaura偶联反应在构造萎缩异构双芳基方面的应用取得了显著进展,但直接构造手性C(芳基)-C(烯烃)轴的化学探索尚不成熟。烯烃取代芳烃底物加剧了反应性、产物构型可萎缩性和选择性控制方面的挑战。

通过精细的配体设计和反应参数的微调,研究人员确定了一种高活性的3,3'-三苯基硅基取代亚磷酸配体,在非常温和的条件下实现受阻芳基卤化物和硼酸乙烯酯的芳烃-烯烃的Suzuki-Miyaura偶合。轴向手性芳基烯烃的生成具有良好的效率、对映选择性和E/Z选择性。

附:英文原文

Title: Asymmetric Construction of Aryl-Alkene Axis by Palladium-Catalyzed Suzuki-Miyaura Coupling Reaction

Author: Sheng-Qi Qiu, Yu Chen, Xiang-Jun Peng, Shi-Jiang He, Jun Kee Cheng, Yong-Bin Wang, Shao-Hua Xiang, Jun Song, Peiyuan Yu, Jun-Min Zhang, Bin Tan

Issue&Volume: 2022-09-16

Abstract: The application of Suzuki-Miyaura coupling reaction to forge the atropisomeric biaryls has seen remarkable progress but exploration of this chemistry to directly forge chiral C(aryl)-C(alkene) axis is underdeveloped. The replacement of arene substrates by alkenes intensifies the challenges in terms of reactivity, configurational atropostability of product and selectivity control. By meticulous ligand design and fine-tuning of reaction parameters, we identified a highly active 3,3'-triphenylsilyl-substituted phosphite ligand to realize arene-alkene Suzuki-Miyaura coupling of hindered aryl halides and vinyl boronates under very mild conditions. The axially chiral acyclic aryl-alkenes were generated in commendable efficiency, enantioselectivity and  E  /  Z  selectivity.

DOI: 10.1002/anie.202211211

Source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202211211

期刊信息

Angewandte Chemie:《德国应用化学》,创刊于1887年。隶属于德国化学会,最新IF:12.959
官方网址:https://onlinelibrary.wiley.com/journal/15213773
投稿链接:https://www.editorialmanager.com/anie/default.aspx