Synlett 2022; 33(18): 1837-1840
DOI: 10.1055/a-1892-4443
cluster
Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

Palladium-Catalyzed Stereospecific Coupling of BINOL-bistriflates and Zinc Cyanide and Applications in the Synthesis of 1,1′-Binaphthyl-2,2′-bisoxazolines (BOXAX)

Zhan Dong
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China
,
Dayou Zhong
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China
,
Zi-Meng Li
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China
,
Wei-Min Liu
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China
,
Jing Zhao
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China
,
Wen-Bo Liu
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China
b   Wuhan University Shenzhen Research Institute, Shenzhen, Guangdong 518000, P. R. of China
› Author Affiliations
We thank the National Natural Science Foundation of China (21971198), the Natural Science Foundation of Hubei Province (2020CFA036), the Fundamental Research Funds for the Central Universities (2042021kf0193), and Guangdong Basic and Applied Basic Research Foundation (2022A1515012614) for financial support.


Abstract

A palladium-catalyzed synthesis of enantiopure [1,1′-binaphthalene]-2,2′-dicarbonitriles from BINOL-bistriflates and zinc cyanide is reported. This cross-coupling reaction employs a 0.1–5 mol% catalyst loading, and is scalable and stereospecific. The synthetic applications of this reaction are demonstrated by product derivatizations and the synthesis of [1,1′-binaphthalene]-2,2′-bisoxazolines (BOXAX).

Supporting Information



Publication History

Received: 10 May 2022

Accepted after revision: 05 July 2022

Accepted Manuscript online:
05 July 2022

Article published online:
28 July 2022

© 2022. Thieme. All rights reserved

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