Efficient Methods for the Synthesis of Arylacetonitriles

Abstract

Various approaches to [2-fluoro-4-(trifluoromethyl)phenyl]acetonitrile were investigated. Two of these methods were selected and applied to a variety of electron-deficient substrates, thereby expanding the scopes of the procedures.

Key words

nitriles - nucleophilic aromatic substitutions - decarboxylations - Wittig reactions - reductions

References

• 1a Lwowski W. In 1,3-Dipolar Cycloaddition Chemistry   Padwa A. Wiley; New York: 1984.  Vol. 1.
• 1b Albert A. Adv. Heterocycl. Chem.  1986,  40:  129 
• 1c Bast K. Christl M. Huisgen R. Mack W. Chem. Ber.  1972,  105:  2825 
• 1d Koguro K. Oga T. Mitsui S. Orita R. Synthesis  1998,  910 
• 1e Finnegan WG. Henry RA. Lofquist R. J. Am. Chem. Soc.  1958,  80:  3908 
• 1f Labbe G. Bruynseels M. Beenaerts L. Vandendriessche A. Delbeke P. Toppet S. Bull. Soc. Chim. Belg.  1989,  98:  343 
• 2 Smith PAS. The Organic Chemistry of Open-Chain Nitrogen Compounds   Vol. 1:  Benjamin; New York: 1965.  Chap. 5. p.209-231  
• 3 Friedrich K. Wallenfels K. In The Chemistry of Cyano Group   Rappoport Z. Wiley-Interscience; New York: 1970.  Chap. 2. p.67-122  
• 4 Harrison IT. Harrison S. In Compendium of Organic Synthetic Methods   Vol. 1:  Wiley; Interscience New York: 1971.  Chap. 13. p.457-478  
• 5 Metzger H. In Methoden der Organischen Chemie (Houben-Weyl)   Vol. 10, Part 4:  Müller E. Thieme; Stuttgart: 1968.  p.217-282  
• 6 Naumov YA. Grandberg II. Russ. Chem. Rev.  1966,  35:  9 
• 7 Starosotnikov AM. Lobach AV. Shevelev SA. Synthesis  2005,  2830 
• 8 Mano T. Stevens RW. Ando K. Kawai M. Kawamura K. Nakao K. Okumura Y. Okumura T. Sakakibara M. Miyamoto K. Tamura T. Chem. Pharm. Bull.  2005,  53:  965 
• 9 Konkel JT. Fan J. Jayachandran B. Kirk KL. J. Fluorine Chem.  2002,  115:  27 
• 10 Clive DLJ. Wang J. J. Org. Chem.  2004,  69:  2773 
• 11 Poschalko A. Welzig S. Treu M. Nerdinger S. Mereiter K. Jordis U. Tetrahedron  2002,  58:  1513 
• 12a Narsaiah AV. Sreenu D. Nagaiah K. Synth. Commun.  2006,  36:  137 
• 12b Yang SH. Chang S. Org. Lett.  2001,  3:  4209 
• 12c Narsaiah AV. Nagaiah K. Adv. Synth. Catal.  2004,  346:  1271 
• 12d Löwe W. Witzel S. Tappmeyer S. Albuschat R. J. Heterocycl. Chem.  2004,  41:  317 
• 12e Movassagh B. Shokri S. Synth. Commun.  2005,  35:  887 
• 12f Miller CP. Kaufman DH. Synlett  2000,  1169 
• 12g Lutz AW, and Diehl RE. inventors; US  4288385.  ; Chem. Abstr. 1981, 96: 103821
• 13a Beare NA. Hartwig JF. J. Org. Chem.  2002,  67:  541 
• 13b Stauffer SR. Beare NA. Stambuli JP. Hartwig JF. J. Am. Chem. Soc.  2001,  123:  4641 
• 14 Kowalczyk BA. Synthesis  1997,  1411 
• 15 Padmavathi V. Balaiah A. Reddy BJM. Padmaja A. Heterocycl. Commun.  2003,  9:  599