Palladium-Catalysed Cross-Coupling of Iodovinylic Acids with Organometallic Reagents. Selective Synthesis of 3,3-Disubstituted Prop-2-enoic Acids

Abstract

3,3-Disubstituted prop-2-enoic acids were selectively prepared in good yields under mild experimental conditions via palladium-catalysed cross-coupling of 3-substituted 3-iodobut-2-enoic acids with miscellaneous organometallic reagents using dichlorobis(acetonitrile)palladium(II) as catalyst and DMF as solvent.

Key words

coupling reactions - carboxylic acids - organozinc reagents - organotin reagents - palladium catalyst

References

• 1a In Comprehensive Organic Synthesis   Vol. 4:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.865-906  
• 1b Nozaki H. In Organometallics in Synthesis   Chap. 8:  Schlosser M. John Wiley; Chichester: 1994.  p.535-578  
• 2a Corey EJ. Katzenellenbogen JA. J. Am. Chem. Soc.  1969,  91:  1851 
• 2b Siddall JB. Biskup M. Fried JH. J. Am. Chem. Soc.  1969,  91:  1853 
• 2c Corey EJ. Katzenellenbogen JA. Posner GH. J. Am. Chem. Soc.  1967,  89:  4245 
• 2d Denmark SE. Jones TK. J. Org. Chem.  1982,  47:  4595 
• 3a Sato F. Ishikawa H. Watanabe H. Miyake T. Sato M. J. Chem. Soc., Chem. Commun.  1981,  718 
• 3b Takagi K. Hayama N. Chem. Lett.  1983,  637 
• 3c Jeffery T. Synthesis  1987,  70 
• 3d Ma S. Lu X. Tetrahedron  1990,  46:  3189 
• 3e Moriarty RM. J. Am. Chem. Soc.  1991,  113:  6315 
• 3f Ma S. Huang X. Lu X. Tetrahedron Lett.  1993,  34:  5963 
• 4a King AO. Okukado N. Negishi E. J. Chem. Soc., Chem. Commun.  1977,  683 
• 4b Stracker EC. Zweifel G. Tetrahedron Lett.  1991,  32:  3329 
• 5 Scott WJ. Crisp GT. Stille JK. J. Am. Chem. Soc.  1984,  106:  4630 
• 6 Stille JK. Simpson JH. J. Am. Chem. Soc.  1987,  109:  2138 
• 7a Trost BM. Nanninga TN. Chan DMT. Organometallics  1982,  1:  1543 
• 7b Lewis FD. Howard DK. Barancyh SV. Oxman JD. J. Am. Chem. Soc.  1986,  108:  3016 
• 7c Ikeda Y. Ukai J. Ikeda N. Yamamoto H. Tetrahedron  1987,  43:  743 
• 7d Beckström P. Jacobson U. Norin T. Tetrahedron  1988,  44:  2541 
• 8a Samuelson B. Angew. Chem., Int. Ed. Engl.  1983,  22:  805 
• 8b Ronning IE. Frank HA. J. Food Prot.  1988,  51:  1643 
• 9 Heathcock CH. In The Total Synthesis of Natural Products   Vol 7:  Apsimon J. Wiley; New York: 1988. 
• 10 Duchêne A. Abarbri M. Parrain JL. Kitamura M. Noyori R. Synlett  1994,  524 
• 11 For initial results see: Abarbri M. Parrain JL. Duchêne A. Tetrahedron Lett.  1995,  36:  2469 
• For the addition of HI on propiolic or tetrolic acids see:
• 12a Bowden K. Price MJ. J. Chem. Soc. B  1970,  1466 
• 12b Chalcat JC. Théron F. Vessière R. C. R. Acad. Sci.  1971,  273:  763 
• 12c Zoller T. Uguen D. Tetrahedron Lett.  1998,  39:  6719 
• For the addition of lithium halides to esters (amides or nitriles) or exclusively on the propiolic acid and phenylpropiolic acid using the LiX/HOAc/solvent/T °C system see:
• 13a Ma S. Lu X. J. Chem. Soc., Chem. Commun.  1990,  1643 
• 13b Ma S. Lu X. Li Z. J. Org. Chem.  1992,  57:  709 
• 13c Meyer C. Marek I. Normant JF. Synlett  1993,  386 
• 13d Piers E. Wong T. Coish P. Rogers C. Can. J. Chem.  1994,  72:  1816 
• 13e Luo F. Hseih L. J. Chin. Chem. Soc.  1994,  41:  871 
• 13f Kotora M. Negishi E. Synthesis  1997,  121 
• For the original use of organozinc reagents in the Pd-catalysed cross-coupling see:
• 15a Negishi E. King AO. Okukad NJ. J. Org. Chem.  1977,  42:  1821 
• 15b King AO. Okukado NJ. Negishi E. J. Chem. Soc., Chem. Commun.  1977,  683 
• 15c Negishi E. Okukado N. King AO. Van Horn DE. Spiegel BI. J. Am. Chem. Soc.  1978,  100:  2254 
• 15d Negishi E. Valente LF. Kobayashi M. J. Am. Chem. Soc.  1980,  102:  3298 
• 15e For a review see: Negishi E. Acc. Chem. Res.  1982,  15:  340 
• 15f See also: Negishi E. Luo FT. Rand CL. Tetrahedron Lett.  1982,  23:  27 
• 15g For methylation of (Z)-3-iodo-2-alken-1-ols see: Negishi E. Zhang Y. Cederbaum FE. Webb MB. J. Org. Chem.  1986,  51:  4080 
• 15h See also: Negishi E. Ay M. Gulevich YV. Noda Y. Tetrahedron Lett.  1993,  34:  1437 
• 15i For a review on organozinc reagents see: Knochel P. Singer RD. Chem. Rev.  1993,  93:  2117 
• 15j In Organozinc Reagents A Practical Approach   Knochel P. Jones P. Oxford University Press; London: 1999. 
• 16a Courtois G. Miginiac L. Bull. Soc. Chim. Fr.  1969,  3330 
• 16b Eisch JJ. Husk GR. J. Am. Chem. Soc.  1965,  87:  4194 
• 16c Felkin H. Tetrahedron Lett.  1966,  875 
• 16d Lehmkuhl H. Reinehr D. J. Organomet. Chem.  1970,  23:  C25 
• 17 Abarbri M. Parrain JL. Kitamura M. Noyori R. Duchêne A. J. Org. Chem.  2000,  657:  475 
• 18 Pereyre M. Quintard JP. Rahm A. In Tin in Organic Synthesis   Butterworths; London: 1987. 
• 19a Stille JK. Angew. Chem., Int. Ed. Engl.  1986,  25:  508 
• 19b Stille JK. Groh BL. J. Am. Chem. Soc.  1987,  109:  813 
• 19c Mitchell TN. Synthesis  1992,  803 
• 19d Farina V. In Comprehensive Organometallic Chemistry II   Vol. 12:  Abel EW. Stone FG. Wilkinson G. Pergamon Press; New York: 1995.  p.Chapter 3.4: 161-241  
• 19e Farina V. Roth GP. In Advances in Metal-Organic Chemistry   Vol. 5:  Liebeskind LS. JAI Press; New York: 1996.  p.1-53  
• 19f Farina V. Krishnamurthy V. Scott WJ. Org. React.  1997,  50:  1, 652 
• 19g Farina V. Krishnamurthy V. In The Stille Reaction   Wiley; New York: 1999. 
• 20a Seyferth D. Stone FGA. J. Am. Chem. Soc.  1957,  79:  515 
• 20b Saihi ML. Pereyre M. Bull. Soc. Chim. Fr.  1977,  1251 
• 21 Cunico RF. Clayton F. J. Org. Chem.  1976,  41:  1480 
• 22a Leusink AJ. Budding HA. J. Organomet. Chem.  1968,  11:  533 
• 22b Launay V. Beaudet I. Quintard JP. Synlett  1997,  821 
• 22c Beaudet I. Launay V. Parrain JL. Quintard JP. Tetrahedron Lett.  1995,  36:  389 
• 23 Thibonnet J. Launay V. Abarbri M. Duchêne A. Parrain J.-L. Tetrahedron Lett.  1998,  39:  4277 

14

We found that these attempts required a higher temperature and removal of the excess acetic acid used was difficult.