Synthesis 2006(15): 2489-2492  
DOI: 10.1055/s-2006-942481
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of Aryl Ferrocenylethynyl Ketones and 2-Ferrocenyl-4H-chromen-4-ones via Palladium-Catalyzed Carbonylation Coupling

Wenbing Maa, Xiaolong Lia, Jingmu Yangb, Zenglu Liuc, Baohua Chen*a, Xinfu Pana
a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: chbh@lzu.edu.cn;
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
c Pharmacy College of Shanghai Jiao Tong University, Shanghai 200030, P. R. of China
Further Information

Publication History

Received 1 March 2006
Publication Date:
11 July 2006 (eFirst)

Abstract

The palladium-catalyzed carbonylation coupling reaction of ethynylferrocene with aryl iodides under an atmosphere of carbon monoxide is a convenient, effective, and versatile method for the synthesis of aryl ferrocenyethynyl ketones. Likewise, the palladium-catalyzed carbonylation coupling-annulation reaction of ethynylferrocene with substituted 2-iodophenol gives 2-ferrocenyl-4H-chromen-4-ones. The reactions were performed in short time and gave the products in good yield.

    References

  • 1 Whittall IR. McDonagh AM. Humphrey MG. Samoc M. Adv. Organomet. Chem.  1998,  42:  291 
  • 2 Greiner A. Bolle B. Hesemann P. Oberski MJ. Sander B. Macromol. Chem. Phys.  1996,  197:  113 
  • 3a Ferrocenes: Homogeneous Catalysis/Organic Synthesis/Materials Science   Togni A. Hayashi T. Wiley-VCH; Weinheim: 1995. 
  • 3b Deschenaux R. Schweissguth M. Vilches M.-T. Levelut A.-M. Hautot D. Long GJ. Luneau D. Organometallics  1999,  18:  5553 ; and references therein
  • 4a Manners I. Pure Appl. Chem.  1999,  71:  1471 
  • 4b Nguyen P. Gomez-Elipe P. Manners I. Chem. Rev.  1999,  99:  1515 
  • 4c Plenio H. Hermann J. Sehring A. Chem. Eur. J.  2000,  6:  1820 
  • 5 Schottenberger H. Wurst K. Buchmeiser RM. J. Organomet. Chem.  1999,  584:  301 ; and references therein
  • 6 Inouye M. Itoh MS. Nakazumi H. J. Org. Chem.  1999,  64:  9393 
  • 7 Yin JX. Wang XJ. Liang YM. Wu XL. Chen BH. Ma YX. Synthesis  2004,  331 
  • 8 Tohda Y. Sonogashira K. Hagihara N. Synthesis  1977,  777 
  • 9 Doisneau G. Balavoine G. Fillebeen-Khan T. J. Organomet. Chem.  1992,  425:  113 
  • 10 Merkushev EB. Synthesis  1988,  923 ; and references therein
  • 11 Edgar JK. Falling NS. J. Org. Chem.  1990,  55:  5287