Get access
Advertisement

[Pd(Ar-BIAN)(alkene)]-Catalyzed Highly Chemo-, Regio-, and Stereoselective Semihydrogenation of 1,2-Allenyl Phosphonates and Related Compounds

Authors

  • Hao Guo,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China, Fax: (+86) 21-6416-7510
    Search for more papers by this author
  • Zilong Zheng,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China, Fax: (+86) 21-6416-7510
    Search for more papers by this author
  • Fei Yu,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China, Fax: (+86) 21-6416-7510
    Search for more papers by this author
  • Shengming Ma Prof.,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China, Fax: (+86) 21-6416-7510
    Search for more papers by this author
  • Alexandre Holuigue,

    1. Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6456
    Search for more papers by this author
  • Dorette S. Tromp,

    1. Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6456
    Search for more papers by this author
  • Cornelis J. Elsevier Prof.,

    1. Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6456
    Search for more papers by this author
  • Yihua Yu

    1. Key Laboratory of Optical and Magnetic Resonance Spectroscopy, East China Normal University, 3663 Zhongshan Road, Shanghai 200062, P. R. China
    Search for more papers by this author

  • The Chinese authors acknowledge financial support from the International Program of the National Natural Science Foundation of China. This research has also been partially funded by the National Research School Combination Catalysis (project number: 2000-14) and by the Universiteit van Amsterdam (grant SAP 2255). We thank Mr. Tao Bai of this group for independently reproducing representative examples of the work reported herein. Ar-BIAN=bis(arylimino)acenaphthene.

Abstract

original image

Often elusive, trisubstituted (Z)-1-alkenyl phosphonates can be prepared by the semihydrogenation of allenyl phosphonates in the presence of Pd complex 1. This reaction, which occurs in high yield with high chemo-, regio-, and stereoselectivity, can be extended to related functionalized allenes and the corresponding Z alkene products (see scheme). R1=H, alkyl, aryl, benzyl; R2,R3=H, alkyl; FG=P(O)(OR)2, P(O)Ph2, SO2Ph, COOEt.

Get access to the full text of this article

Ancillary