Citation: Guodong Wang, Mengying Jia, Haitao Liu, Yong Liu, Zhiguo Zhang, Xianxiu Xu. Expeditious synthesis and applications of isoquinoline ring-modified Quinap derivatives[J]. Chinese Chemical Letters, ;2025, 36(8): 110705. doi: 10.1016/j.cclet.2024.110705 shu

Expeditious synthesis and applications of isoquinoline ring-modified Quinap derivatives

Guodong Wang ^a ,
Mengying Jia ^{a, *,} ,
Haitao Liu ^a ,
Yong Liu ^a ,
Zhiguo Zhang ^{b, *,} ,
Xianxiu Xu ^{a, *,}

a.
College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Institute of Molecular and Nano Science, Shandong Normal University, Ji'nan 250014, China
b.
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

jiamy231@sdnu.edu.cn

zhangzg@htu.edu.cn

xuxx677@sdnu.edu.cn

Received Date: 29 August 2024
Revised Date: 25 November 2024
Accepted Date: 2 December 2024
Available Online: 2 December 2024

Figures(5)

A wide range of isoquinoline ring-modified Quinap oxides with different steric and electronic variations have been constructed through a palladium-catalyzed imidoylative cyclization of arylethenyl isocyanides with 2-diphenylphosphinyl-1-naphthyl bromides. The Pd-catalysis plays dual roles in the formation of both axial C–C bond and isoquinoline ring. This de novo synthetic strategy features good functional group tolerance, high yields and easy scale-up, providing Quinap derivatives with substitution patterns that could not be obtained using coupling reactions. Chiral ligands 7 and 12 can be readily prepared by transformation of the resulting Quinap oxide to their BINOL esters, and have been proven to be superb chiral ligands for the copper-catalyzed enantioselective A³-coupling and alkynylation of quinoline reactions. In general, the enantioselectivies obtained using ligands 7 and 12 are excellent, and the ee values are higher than those using Quinap as ligand, even three times higher in some cases. Mechanism studies revealed that a monomeric copper(Ⅰ) complex bearing a single chiral ligand was formed and served as the catalytically active species.
- Isocyanides,
- Domino reactions,
- Quinap ligands,
- Enantioselective A³ coupling,
- Asymmetric catalysis
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