Synthesis 2019; 51(17): 3269-3276
DOI: 10.1055/s-0037-1610712
paper
© Georg Thieme Verlag Stuttgart · New York

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

Ze-Zhen Jiang
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: xubin@shu.edu.cn
b   State 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
b   State 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
b   State 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
b   State 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
,
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: xubin@shu.edu.cn
b   State 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*
a   Department 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*
b   State 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
c   Shanghai-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
› Author Affiliations
We acknowledge financial support from the National Natural Science Foundation of China (NSFC) (grants 21772215, 21532010 and 21472214), the Strategic Priority Research Program of the Chinese Academy of Sciences (grant XDB20030100), the NSFC and the Research Grants Council of Hong Kong Joint Research Scheme (grant 21361162001), the Chinese Academy of Sciences, the Technology Commission of Shanghai Municipality and the Croucher Foundation of Hong Kong.
Further Information

Publication History

Received: 18 March 2019

Accepted after revision: 15 April 2019

Publication Date:
14 May 2019 (online)


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.

Supporting Information

 
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