Asymmetric Construction of an Aryl‐Alkene Axis by Palladium‐Catalyzed Suzuki–Miyaura Coupling Reaction

Autor: Sheng‐Qi Qiu, Yu Chen, Xiang‐Jun Peng, Shi‐Jiang He, Jun Kee Cheng, Yong‐Bin Wang, Shao‐Hua Xiang, Jun Song, Peiyuan Yu, Junmin Zhang, Bin Tan
Rok vydání: 2022
Předmět:
Zdroj: Angewandte Chemie International Edition. 61
ISSN: 1521-3773
1433-7851
DOI: 10.1002/anie.202211211
Popis: 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.
Databáze: OpenAIRE
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