Palladium-Catalyzed Asymmetric Heck–Matsuda Reaction of 1,4-Dihydroquinolines with Aryl Diazonium Salts

Ze-Zhen Jiang; Yang-Jie Jiang; Juan Du; Di Chen; Chang-Hua Ding; Bin Xu; Xue-Long Hou

doi:10.1055/s-0037-1610712

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(17): 3269-3276
DOI: 10.1055/s-0037-1610712

paper

Palladium-Catalyzed Asymmetric Heck–Matsuda Reaction of 1,4-Dihydroquinolines with Aryl Diazonium Salts

Authors

Ze-Zhen Jiang

^aDepartment of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: xubin@shu.edu.cn

^bState Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Yang-Jie Jiang

^bState Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Juan Du

^bState Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Di Chen

^bState Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Chang-Hua Ding *

^aDepartment of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: xubin@shu.edu.cn

^bState Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Bin Xu*

^aDepartment of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China eMail: dingchanghua@shu.edu.cn eMail: xubin@shu.edu.cn
Xue-Long Hou*

^bState Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

^cShanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: xlhou@sioc.ac.cn

Abstract

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Abstract

A palladium-catalyzed asymmetric Heck–Matsuda reaction of N-Boc-1,4-dihydroquinolines and aryl diazonium tetrafluoroborates is realized in moderate to high yields and with high enantioselectivities. The method provides an efficient route to access optically active 2-arylhydroquinolines.

Key words

palladium - Heck–Matsuda reaction - asymmetric catalysis - 1,4-dihydroquinolines - aryl diazonium tetrafluoroborates - 2-arylhydroquinolines

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Referenzen

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