On the Synthesis of Arylpropiolic Acids and Investigations towards the Formation of Vinyl Chlorides by HCl Addition During Esterification Reactions

Abstract

The synthesis protocol for the preparation of different arylpropiolic acids using the Negishi reaction and the addition of HCl to the alkyne moiety of these acids in subsequent esterification reactions using SOCl₂ was examined.

Key words

alkynes - esterification - addition reactions - vinyl chlorides - Negishi reaction

References

• 1a Brandsma L. Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques   Elsevier/Academic Press; Amsterdam: 2003. 
• 1b Acetylene Chemistry   Diederich F. Stang PJ. Tykwinski RR. Wiley-VCH; Weinheim: 2005. 
• Recent reviews on functionalized alkynes: Ynolates:
• 2a Shindo M. Tetrahedron  2007,  63:  10 
• Alkynylphosphines:
• 2b Kondoh A. Yorimitsu H. Oshima K. Chem. Asian J.  2010,  5:  398 
• Ynamides:
• 2c Evano G. Coste A. Jouvin K. Angew. Chem. Int. Ed.  2010,  49:  2840 
• 2d DeKorver KA. Li H. Lohse AG. Hayashi R. Lu Z. Zhang Y. Hsung RP. Chem. Rev.  2010,  110:  5064 
• 3 Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
• 4 Recent example from our group: Hapke M. Kral K. Fischer C. Spannenberg A. Gutnov A. Redkin D. Heller B. J. Org. Chem.  2010,  75:  3993 
• 5 Otera J. Nishikido J. Esterification   2nd ed.:  Wiley-VCH; Weinheim: 2010. 
• The organozinc reagent was prepared by lithiation of ethyl propiolate with LDA, followed by subsequent transmetallation with anhyd ZnCl₂. We also investigated the application of direct zincation of ethyl propiolate following a reported literature protocol. However, the procedure did not work out well in our hands for this case:
• 6a Anastasia L. Negishi E. Org. Lett.  2001,  3:  3111 
• 6b The superiority of the Negishi vs. the Sonogashira protocol for the coupling of electron-deficient alkynes with alkenyl halides has been investigated earlier: Negishi E. Mingxing Q. Fanxing Z. Anastasia L. Babinski D. Org. Lett.  2003,  5:  1597 
• Earlier detailed studies:
• 8a Adams R. Ludington RS.
  J. Am. Chem. Soc.  1945,  67:  794 
• 8b Bowden K. Price MJ. J. Chem. Soc. B  1970,  1466 
• 8c Bowden K. Price MJ. J. Chem. Soc. B  1970,  1472 
• 9 Urdaneta NA. Herrera JC. Salazar J. López SE. Synth. Commun.  2002,  32:  3003 
• 10 Urdaneta NA. Salazar J. Herrera JC. López SE. Synth. Commun.  2004,  34:  657 
• 11 Medvedeva AS. Andreev MV. Safronova LP. Afonin AV. Russ. J. Org. Chem.  2005,  41:  1493 
• 12 Klapars A. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  14844 
• 13 Saraf SD. Zaki M. Synthesis  1973,  612 
• 14 Hegedus LS. In Organometallics in Synthesis   Schlosser M. Wiley; Chichester: 1997.  p.448 
• 15 Khurana JM. Chauhan S. Bansal G. Monatsh. Chem.  2004,  135:  83 
• 16 Shibata Y. Hirano M. Tanaka K. Org. Lett.  2008,  10:  2829 
• 17 Müller G. Wessig P. Chem. Commun.  2006,  4524 
• 18 The acid chloride 4 was mentioned in the literature, however, no spectral data were given: Imase H. Suda T. Shibata Y. Noguchi K. Hirano M. Tanaka K. Org. Lett.  2009,  11:  1805 
• 19 Suzuki H. Kondo A. Inouye M. Ogawa T. Synthesis  1986,  121 
• 20a van Veldhuizen A. van Dijk M. Sanders GM. Org. Magn. Reson.  1980,  13:  105 
• 20b Zoltewicz JA. Maier NM. Lavieri S. Ghiviriga I. Abboud KA. Fabian WMF. Tetrahedron  1997,  53:  5379 
• 21 Yadav JS. Reddy BVS. Reddy PSR. Basak AK. Narsaiah AV. Adv. Synth. Catal.  2004,  346:  77 
• 22 Chenault J. Dupin J.-FE. Synthesis  1987,  498 
• 23a Forsyth DA. Spear RJ. Olah GA. J. Am. Chem. Soc.  1976,  98:  2512 
• 23b Yamamoto H. Maruoka K. J. Am. Chem. Soc.  1981,  103:  6133 
• 24 Noro M. Masuda T. Ichimura AS. Koga N. Iwamura H. J. Am. Chem. Soc.  1994,  116:  6179 
• 25 Aitken RA. Horsburgh ER. McCreadie JG. Seth S. J. Chem. Soc., Perkin Trans. 1  1994,  1727 
• 26 General synthetic procedure: Molander GA. Biolatto B. J. Org Chem.  2003,  68:  4302 
• 27 General synthetic procedure: Ali NM. McKillop A. Mitchell MB. Rebelo RA. Wallbank PJ. Tetrahedron  1992,  48:  8117 

7

The crystallographic data for compound 6 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 797405. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: [phone]; e-mail: [e-mail]].