Olefination Reactions Using Tetraarylphosphonium (TAP)-Supported Phosphorus Ylides

Abstract

Tetraarylphosphonium (TAP)-supported phosphorus ylides were prepared and used in copper-catalyzed olefination reactions with diazo compounds to produce conjugated esters, amides, and phosphonates. The TAP-phosphine oxide can easily be separated from the alkene product, recycled, and reused.

Key words

alkenes - diazo compounds - green chemistry - Wittig reaction - ylides

References

• 1 Takeda T. Modern Carbonyl Olefination   Wiley-VCH; Weinheim: 2004. 
• 2a Wittig G. Geissler G. Liebigs Ann. Chem.  1953,  580:  44 
• 2b Wittig G. Schöllkopf U. Chem. Ber.  1954,  87:  1318 
• 3a Nicolaou KC. Harter MW. Gunzner JL. Nadin A. Liebigs Ann. Chem.  1997,  1283 
• 3b Murphy PJ. Lee SE. J. Chem. Soc., Perkin Trans. 1  1999,  3049 
• 3c Rein T. Pedersen TM. Synthesis  2002,  579 
• 3d Ramazani A. Kazemizadeh AR. Ahmadi E. Noshiranzadeh N. Souldozi A. Curr. Org. Chem.  2008,  12:  59 
• 4 Constable DJC. Dunn PJ. Hayler JD. Humphrey GR. Leazer JL. Linderman RJ. Lorenz K. Manley J. Pearlman BA. Wells A. Zaks A. Zhang TY. Green Chem.  2007,  9:  411 
• 5a Clarke SD. Harrison CR. Hodge P. Tetrahedron Lett.  1980,  21:  1375 
• 5b Bernard M. Ford WT. J. Org. Chem.  1983,  48:  326 
• 5c Bernard M. Ford WT. Nelson EC. J. Org. Chem.  1983,  48:  3164 
• 5d Sieber F. Wentworth P. Toker JD. Wentworth AD. Metz WA. Reed NN. Janda KD. J. Org. Chem.  1999,  64:  5188 
• 5e Westman J. Org. Lett.  2001,  3:  3745 
• 5f Fairlamb IJS. ChemSusChem  2009,  2:  1021 
• 5g Marsden SP. Nat. Chem.  2009,  1:  685 
• 5h O’Brien CJ. Tellez JL. Nixon ZS. Kang LJ. Carter AL. Kunkel SR. Przeworski KC. Chass GA. Angew. Chem. Int. Ed.  2009,  48:  6836 
• 5i Leung PSW. Teng Y. Toy PH. Org. Lett.  2010,  12:  4996 
• 6a Poupon JC. Boezio AA. Charette AB. Angew. Chem. Int. Ed.  2006,  45:  1415 
• 6b Zoute L. Lacombe C. Quirion JC. Charette AB. Jubault P. Tetrahedron Lett.  2006,  47:  7931 
• 7a Kuhn FE. Santos AM. Mini-Rev. Org. Chem.  2004,  1:  55 
• 7b Lebel H. Paquet V. J. Am. Chem. Soc.  2004,  126:  320 
• 7c Sun W. Kuhn FE. Appl. Catal., A  2005,  285:  163 
• 7d Sun W. Yu BS. Kuhn FE. Tetrahedron Lett.  2006,  47:  1993 
• 7e Pedro FM. Santos AM. Baratta W. Kuhn FE. Organometallics  2007,  26:  302 
• 7f Lebel H. Ladjel C. Organometallics  2008,  27:  2676 
• 8a Lebel H. Davi M. Diez-Gonzalez S. Nolan SP.
  J. Org. Chem.  2007,  72:  144 
• 8b Lebel H. Ladjel C. Brethous L. J. Am. Chem. Soc.  2007,  129:  13321 
• 8c Lebel H. Parmentier M. Org. Lett.  2007,  9:  3563 
• 8d Lebel H. Davi M. Adv. Synth. Catal.  2008,  350:  2352 
• 8e Lebel H. Davi M. Stoklosa GT. J. Org. Chem.  2008,  73:  6828 
• 8f Davi M. Lebel H. Org. Lett.  2009,  11:  41 
• 10 Shriver DF. Drezdzon MA. The Manipulation of Air-Sensitive Compounds   Wiley; New York: 1986. 
• 11 Searle NE. Org. Synth. Coll. Vol. IV   Wiley; New York: 1963.  p.424 
• 12 Bartlett PA. Carruthers NI. Winter BM. Long KP. J. Org. Chem.  1982,  47:  1284 
• 13 Ohira S. Synth. Commun.  1989,  19:  561 
• 14 Still WC. Kahn M. Mitra A. J. Org. Chem.  1978,  43:  2923 
• 16 Artuso E. Barbero M. Degani I. Dughera S. Fochi R. Tetrahedron  2006,  62:  3146 
• 17 Rai R. Katzenellenbogen JA. J. Med. Chem.  1992,  35:  4150 
• 18 Felluga F. Pitacco G. Valentin E. Venneri CD. Tetrahedron: Asymmetry  2008,  19:  945 

9

Although the crude NMR spectra showed >90% product purity, flash chromatography was performed to remove diethyl fumarate and maleate formed from ethyl diazoacetate.

15

When unreacted aldehyde was present, the filtrate was stirred with aq 10% NaHSO₃ (3 mL) at r.t. for 1 h. The two layers were separated and the organic layer was washed with H₂O (3 mL), dried (MgSO₄), and concentrated under reduced pressure to afford a pure mixture of E- and Z-olefin isomers.