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 (eFirst)

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

 
  • References


    • For selected examples, see:
    • 2a Amat M. Pérez M. Bosch J. Synlett 2011; 143
    • 2b Barthel C. Sorger D. Deuther-Conrad W. Scheunemann M. Schweiger S. Jäckel P. Roghani A. Steinbach J. Schüürmann G. Sabri O. Brust P. Wenzel B. Eur. J. Med. Chem. 2015; 100: 50
    • 2c Sparano BA. Shahi SP. Koide K. Org. Lett. 2004; 6: 1947
    • 2d Gitto R. De Luca L. Ferro S. Scala A. Ronsisvalle S. Parenti C. Prezzavento O. Buemi MR. Chimirri A. Bioorg. Med. Chem. 2014; 22: 393
    • 4a Patil NT. Kavthe RD. Shinde VS. Tetrahedron 2012; 68: 8079
    • 4b Nakamura I. Yamamoto Y. Chem. Rev. 2004; 104: 2127
    • 4c Müller TE. Hultzsch KC. Yus M. Foubelo F. Tada M. Chem. Rev. 2008; 108: 3795

      For selected reviews on palladium-catalyzed coupling reactions, see:
    • 5a Alonso F. Beletskaya IP. Yus M. Tetrahedron 2008; 64: 3047
    • 5b Negishi E. Anastasia L. Chem. Rev. 2003; 103: 1979
    • 5c Surry DS. Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
    • 5d Doucet H. Hierso J.-C. Angew. Chem. Int. Ed. 2007; 46: 834
    • 5e Enthaler S. Company A. Chem. Soc. Rev. 2011; 40: 4912
    • 5f Kambe N. Iwasaki T. Terao J. Chem. Soc. Rev. 2011; 40: 4937
    • 5g Knappke CE. I. Jacobi von Wangelin A. Chem. Soc. Rev. 2011; 40: 4948
    • 5h Molnár Á. Chem. Rev. 2011; 111: 2251
    • 5i Selander N. Szabó KJ. Chem. Rev. 2011; 111: 2048

      For reviews, see:
    • 6a Vlarr T. Ruijter E. Orru RV. A. Adv. Synth. Catal. 2011; 353: 809
    • 6b Wu X.-F. Neumann H. Beller M. Chem. Rev. 2013; 113: 1
    • 6c Beccalli EM. Broggini G. Martinelli M. Sottocornola S. Chem. Rev. 2007; 107: 5318
    • 6d Zeni G. Larock RC. Chem. Rev. 2006; 106: 4644
    • 6e Majumdar KC. Chattopadhyay B. Maji PK. Chattopadhyay SK. Samanta S. Heterocycles 2010; 81: 517
    • 6f Majumdar KC. Samanta S. Sinha B. Synthesis 2012; 44: 817

      Selected examples for the synthesis of piperidines catalyzed by palladium, see:
    • 7a Yoshida M. Kinoshita K. Namba K. Org. Biomol. Chem. 2014; 12: 2394
    • 7b Xie Z. Wu P. Cai L. Tong X. Tetrahedron Lett. 2014; 55: 2160
    • 8a Shen K. Han X. Lu X. Org. Lett. 2013; 15: 1732
    • 8b Shen K. Han X. Xia G. Lu X. Org. Chem. Front. 2015; 2: 145

      For reviews, see:
    • 9a Ketcham JM. Shin I. Montgomery TP. Krische MJ. Angew. Chem. Int. Ed. 2014; 53: 9142
    • 9b Moran J. Krische MJ. Pure Appl. Chem. 2012; 84: 1729
    • 9c Bower JF. Kim IS. Patman RL. Krische MJ. Angew. Chem. Int. Ed. 2009; 48: 34
  • 10 CCDC 1534327 (2a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.