Synthesis 2017; 49(20): 4687-4692
DOI: 10.1055/s-0036-1588803
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Substituted Piperidines via Cationic Palladium(II)-Catalyzed Reductive Coupling of N-Tosyl-Tethered Alkynones

Xiaojuan Zhang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China   Email: xlhan@mail.sioc.ac.cn   Email: xylu@mail.sioc.ac.cn
,
Xiuling Han*
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China   Email: xlhan@mail.sioc.ac.cn   Email: xylu@mail.sioc.ac.cn
,
Zhiyong Hu
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China   Email: xlhan@mail.sioc.ac.cn   Email: xylu@mail.sioc.ac.cn
,
Xiyan Lu*
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China   Email: xlhan@mail.sioc.ac.cn   Email: xylu@mail.sioc.ac.cn
› Author Affiliations
Supported by: We thank the National Natural Science Foundation of China (21232006, 21642002) and the Chinese Academy of Sciences for financial support.
Further Information

Publication History

Received: 06 March 2017

Accepted after revision: 30 March 2017

Publication Date:
03 May 2017 (online)


Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis

Abstract

A cationic palladium(II) complex catalyzed reductive coupling of N-tosyl-tethered alkynones for the synthesis of functionalized piperidines was successfully developed. This reaction was initiated by hydropalladation of the alkyne and quenched by addition to the intramolecular carbonyl group. The substituent on the alkyne is key to the reaction.

Supporting Information

 
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