Synlett 2012; 23(10): 1497-1500
DOI: 10.1055/s-0031-1290676
letter
© Georg Thieme Verlag Stuttgart · New York

Mild Oxidation of Benzylic Amines into Aldehydes Using an Oxidative Polonovski-Like Process

Samuel Desjardins
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada, Fax: +1(514)9874054   Email: [email protected]
,
Guillaume Jacquemot
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada, Fax: +1(514)9874054   Email: [email protected]
,
Sylvain Canesi*
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada, Fax: +1(514)9874054   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 03 March 2012

Accepted after revision: 02 April 2012

Publication Date:
25 May 2012 (online)


Abstract

A chemoselective and environmentally benign oxidation of benzylic amines into aldehydes mediated by a hypervalent iodine reagent has been developed. This mild oxidative version of the ­Polonovski process may be selectively carried out in the presence of several functionalities including a free alcohol and provides new synthetic opportunities as a masked aldehyde segment.

 
  • References

    • 1a Davis L, Metzler DE In The Enzymes . 3rd ed., Vol. 7. Academic Press; New York: 1972: 33-65
    • 1b Rawalay SS, Schechter H. J. Org. Chem. 1967; 32: 3129
    • 1c Noureldin NA, Bellegarde JW. Synthesis 1999; 939
    • 1d Audette RJ, Quail JW, Smith PJ. Tetrahedron Lett. 1971; 12: 27
    • 1e Stephens FF, Bower JD. J. Chem. Soc. 1949; 2971
    • 1f Nakagawa K, Onoue H, Sugita J. Chem. Pharm. Bull. 1964; 12: 1135
    • 1g Orito K, Hatakeyama T, Takeo M, Uchiito S, Tokuda M, Suginome H. Tetrahedron 1998; 54: 8403
    • 1h Chen HG, Knochel P. Tetrahedron Lett. 1988; 29: 6701
    • 1i Buckley TF, Rapoport H. J. Am. Chem. Soc. 1982; 104: 4446
    • 1j Matuo J, Kawana A, Fukuda Y, Mukaiyama T. Chem. Lett. 2001; 712
    • 1k Miyazawa A, Tanaka K, Sakakura T, Tashiro M, Tashiro H, Prakash GK. S, Olah GA. Chem. Commun. 2005; 2104
    • 1l Hoffman RV. J. Am. Chem. Soc. 1976; 98: 6702
    • 1m Lee GA, Freedman HH. Tetrahedron Lett. 1976; 17: 1641
    • 1n Hu Y, Hu H. Synth. Commun. 1992; 22: 1491
    • 1o Hamamoto H, Suzuki Y, Takahashi H, Ikegami S. Tetrahedron Lett. 2007; 48: 4239
    • 1p Rajalakshmi V, Vijayaraghavan VR, Varghese B, Raghavan A. Inorg. Chem. 2008; 47: 5821
    • 1q Sharma S, Barooah N, Baruah JB. J. Mol. Catal. A: Chem. 2005; 229: 171
    • 1r Knowles DA, Mathews CJ, Tomkinson NC. O. Synlett 2008; 2769
    • 1s Chu G, Li C. Org. Biomol. Chem. 2010; 8: 4716
    • 1t Liu L, Zhang S, Fu X, Yan C.-H. Chem. Commun. 2011; 47: 10148
    • 2a Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, In Topics in Current Chemistry. Wirth T. Ed.; Springer; Berlin: 2003: 224
    • 2b Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
    • 2c Zhdankin VV. ARKIVOC 2009; (i): 1
    • 2d Bérard D, Giroux MA, Racicot L, Sabot C, Canesi S. Tetrahedron 2008; 753
    • 2e Sabot C, Bérard D, Canesi S. Org. Lett. 2008; 10: 4629
    • 2f Sabot C, Commare B, Nahi S, Duceppe MA, Guérard KC, Canesi S. Synlett 2008; 3226
    • 2g Guérard KC, Sabot C, Racicot L, Canesi S. J. Org. Chem. 2009; 74: 2039
    • 2h Sabot C, Guérard KC, Canesi S. Chem. Commun. 2009; 2941
    • 2i Guérard KC, Chapelle C, Giroux MA, Sabot C, Beaulieu MA, Achache N, Canesi S. Org. Lett. 2009; 11: 4756
    • 2j Dohi T, Kita Y. Chem. Commun. 2009; 2073
    • 2k Dohi T, Ito M, Yamaoka N, Morimoto K, Fujioka H, Kita Y. Tetrahedron 2009; 65: 10797
    • 2l Guérard KC, Sabot C, Beaulieu MA, Giroux MA, Canesi S. Tetrahedron 2010; 66: 5893
    • 2m Andrez JA, Giroux MA, Lucien J, Canesi S. Org. Lett. 2010; 12: 4368
    • 2n Beaulieu MA, Sabot C, Achache N, Guérard KC, Canesi S. Chem. Eur. J. 2010; 16: 11224
    • 2o Desjardins S, Andrez JA, Canesi S. Org. Lett. 2011; 13: 3406
    • 2p Beaulieu MA, Guérard KC, Maertens G, Sabot C, Canesi S. J. Org. Chem. 2011; 76: 9460
    • 2q Dohi T, Kato D, Hyodo R, Yamashita D, Shiro M, Kita Y. Angew. Chem. Int. Ed. 2011; 50: 3784
    • 2r Guérard KC, Guerinot A, Bouchard-Aubin C, Ménard MA, Lepage M, Beaulieu MA, Canesi S. J. Org. Chem. 2012; 77: 2121
    • 3a Pelter A, Drake RA. Tetrahedron Lett. 1988; 29: 4181
    • 3b Quideau S, Looney MA, Pouységu L. J. Org Chem. 1998; 63: 9597
    • 3c Ozanne-Beaudenon A, Quideau S. Angew. Chem. Int. Ed. 2005; 44: 7065
    • 3d Ciufolini MA, Canesi S, Ousmer M, Braun NA. Tetrahedron 2006; 62: 5318
    • 3e Bérard D, Jean A, Canesi S. Tetrahedron Lett. 2007; 48: 8238
    • 3f Jean A, Cantat J, Bérard D, Bouchu D, Canesi S. Org. Lett. 2007; 9: 2553
    • 3g Pouységu L, Chassaing S, Dejugnac D, Lamidey AM, Miqueu K, Sotiropoulos JM, Quideau S. Angew. Chem. Int. Ed. 2008; 47: 3552
    • 3h Bérard D, Racicot L, Sabot C, Canesi S. Synlett 2008; 1076
    • 3i Pouységu L, Marguerit M, Gagnepain J, Lyvinec G, Eatherton AJ, Quideau S. Org. Lett. 2008; 10: 5211
    • 3j Mendelsohn BA, Lee S, Kim S, Teyssier F, Aulakh VS, Ciufolini MA. Org. Lett. 2009; 11: 1539
    • 3k Quideau S, Lyvinec G, Marguerit Bathany K, Ozanne-Beaudenon A, Bufeteau T, Cavagnat D, Chenede A. Angew. Chem. Int. Ed. 2009; 48: 4605
    • 3l Giroux MA, Guérard KC, Beaulieu MA, Sabot C, Canesi S. Eur. J. Org. Chem. 2009; 3871
    • 3m Traoré M, Ahmed-Ali S, Peuchmaur M, Wong YS. Tetrahedron 2010; 66: 5863
    • 3n Liang H, Ciufolini MA. Tetrahedron 2010; 66: 5884
    • 3o Pouységu L, Sylla T, Garnier T, Rojas LB, Charris J, Deffieux D, Quideau S. Tetrahedron 2010; 66: 5908
    • 4a Polonovski M, Polonovski M. Bull. Soc. Chim. Fr. 1927; 41: 1190
    • 4b Ahond A, Cave A, Kan-Fan C, Husson HP, de Rostolan J, Potier P. J. Am. Chem. Soc. 1968; 90: 5622
    • 4c Grierson D. Org. React. 1990; 39: 85
  • 5 Son YW, Kwon TH, Lee JK, Pae AN, Lee JY, Cho YS, Min S. J. Org. Lett. 2011; 13: 6500
  • 6 Sakakura A, Ohkubo T, Yamashita R, Akakura M, Ishihara K. Org. Lett. 2011; 13: 892

    • For NMR data of compound 8f and compound 8g, see:
    • 7a Kotha S, Behera M, Shah VR. Synlett 2005; 1877
    • 7b Lazzarato L, Donnola M, Rolando B, Chegaev K, Marini E, Cena C, Di Stilo A, Fruttero R, Biondi S, Ongini E, Gasco A. J. Med. Chem. 2009; 52: 5058
    • 8a Pummerer R. Ber. Dtsch. Chem. Ges. 1910; 43: 1401
    • 8b Padwa A, Waterson AG. Curr. Org. Chem. 2000; 4: 175
  • 9 Koser GF, Wettach RH. J. Org. Chem. 1977; 42: 1476