Synthesis 2011(14): 2303-2309  
DOI: 10.1055/s-0030-1260060
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Molybdenum Hexacarbonyl Mediated Alkoxycarbonylation of Aryl Halides

Wei Ren, A. Emi, Motoki Yamane*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
Fax: +65(6791)1961; e-Mail: yamane@ntu.edu.sg;
Further Information

Publication History

Received 22 March 2011
Publication Date:
09 June 2011 (online)

Abstract

Mo(CO)6-mediates the alkoxycarbonylation of aryl halides in their reaction with alcohols to afford arenecarboxylic acid esters. The molybdenum carbonyl complexes act as the catalyst and the source with carbon monoxide. The alkoxycarbonylation proceeds with a small excess of carbon monoxide in the form of Mo(CO)6 and the procedure is simple compared to the conventional method, which uses palladium catalyst under gaseous carbon monoxide. Using this procedure, a variety of carboxylic acid esters were prepared.

    References

  • 1a Schoenberg A. Bartoletti I. Heck RF. J. Org. Chem.  1974,  39:  3318 
  • 1b Schoenberg A. Heck RF. J. Org. Chem.  1974,  39:  3327 
  • 1c Schoenberg A. Heck RF.
    J. Am. Chem. Soc.  1974,  96:  7761 
  • For palladium-catalyzed carbonylation, see:
  • 2a Colquhoun HM. Thompson DJ. Twigg MV. Carbonylation, Direct Synthesis of Carbonyl Compounds   Plenum Press; New York: 1991. 
  • 2b Gulevich YV. Bumagin NA. Beletskaya IP. Russ. Chem. Rev. (Engl. Transl.)  1988,  57:  299 
  • 2c Beller M. Cornils B. Frohning CD. Kohlpaintner CW. J. Mol. Catal.  1995,  104:  17 
  • 2d Stromnova TA. Moiseev II. Russ. Chem. Rev. (Engl. Transl.)  1998,  67:  485 
  • 2e Skoda-Földes R. Kollár L. Curr. Org. Chem.  2002,  6:  1097 
  • 2f Barnard CFJ. Organometallics  2008,  27:  5402 
  • 2g Brennführer A. Neumann H. Beller M. Angew. Chem. Int. Ed.  2009,  48:  4114 
  • For palladium-catalyzed alkoxycarbonylation, see:
  • 3a Mori M. In Handbook of Organopalladium Chemistry for Organic Synthesis   Vol. 2:  Negishi E. Wiley-Interscience; New York: 2000.  p.2663 
  • 3b Beller M. In Applied Homogeneous Catalysis with Organometallic Compounds   2nd ed., Vol. 1:  Cornils B. Herrmann WA. Wiley-VCH; Weinheim: 2002.  p.145 
  • For selected recent examples, see:
  • 3c Neumann H. Brennführer A. Groß P. Riermeier T. Almena J. Beller M. Adv. Synth. Catal.  2006,  348:  1255 
  • 3d Jimenez-Rodriguez C. Eastham GR. Cole-Hamilton DJ. Dalton Trans.  2005,  10:  1826 
  • 3e Cai MZ. Zhao H. Huang YX. J. Mol. Catal. A: Chem.  2005,  238:  41 
  • 3f Iannelli M. Bergamelli F. Kormos CM. Paravisi S. Leadbeater NE. Org. Process Res. Dev.  2009,  13:  634 
  • 3g Salvadori J. Balducci E. Zaza S. Petricci E. Taddei M. J. Org. Chem.  2010,  75:  1841 
  • For a review, see:
  • 4a Morimoto T. Kakiuchi K. Angew. Chem. Int. Ed.  2004,  43:  5580 
  • For using aldehyde as the substitute for CO gas, see:
  • 4b Morimoto T. Fujioka M. Fuji K. Tsutsumi K. Kakiuchi K. Chem. Lett.  2003,  32:  154 
  • 4c Morimoto T. Fujioka M. Fuji K. Tsutsumi K. Kakiuchi K. J. Organomet. Chem.  2007,  692:  625 
  • For using formamide, see:
  • 4d Wan YQ. Alterman M. Larhed M. Hallberg A. J. Comb. Chem.  2003,  5:  82 
  • For using DMF, see:
  • 4e Hosoi K. Nozaki K. Hiyama T. Org. Lett.  2002,  4:  2849 
  • 4f Wan YQ. Alterman M. Larhed M. Hallberg A. J. Org. Chem.  2002,  67:  6232 
  • 4g Ju J. Jeong M. Moon J. Jung HM. Lee S. Org. Lett.  2007,  9:  4615 
  • 4h Tambade PJ. Patil YP. Bhanushali MJ. Bhanage BM. Tetrahedron Lett.  2008,  49:  2221 
  • For using CHCl3, see:
  • 4i Grushin VV. Alper H. Organometallics  1993,  12:  3846 
  • For using acetic formic anhydride, see:
  • 4j Cacchi S. Fabrizi G. Goggiamani A. Org. Lett.  2003,  5:  4269 
  • For using AcCl, see:
  • 4k Hermange P. Lindhardt AT. Taaning RH. Bjerglund K. Lupp D. Skrydstrup T. J. Am. Chem. Soc.  2011,  133:  6061 
  • 5a Kaiser N.-FK. Hallberg A. Larhed M. J. Comb. Chem.  2002,  4:  109 
  • 5b Wan Y. Alterman M. Larhed M. Hallberg A. J. Org. Chem.  2002,  67:  6232 
  • 5c Wannbeg J. Larhed M. J. Org. Chem.  2003,  68:  5750 
  • 5d Wan Y. Alterman M. Larhed M. Hallberg A. J. Comb. Chem.  2003,  5:  82 
  • 6 Ren W. Yamane M. J. Org. Chem.  2010,  75:  8410 
  • 7 Recently, Roberts and co-workers reported the Mo-mediated carbonylation of aryl halides with various nucleophiles under microwave irradiation. They used Mo(CO)6 (1.0 equiv) with respect to the aryl halides, see: Roberts B. Liptrot D. Alcaraz L. Luker T. Stocks MJ. Org. Lett.  2010,  12:  4280 
  • 9 Zippi EM. Synth. Commun.  1994,  24:  2515 
  • 10 Khan KM. Maharvi GM. Hayat S. . Choudhary MI. . Tetrahedron  2003,  59:  5549 
  • 11 Arrowsmith GB. Jeffery GH. Vogel AI. J. Chem. Soc.  1965,  2072 
  • 12 Wiles C. Watts P. Haswell SJ. Tetrahedron Lett.  2006,  47:  5261 
  • 13 Ramesh C. Nakamura R. Kubota Y. Miwa M. Sugi Y. Synthesis  2003,  501 
  • 14 Liu Z. Larock RC. J. Org. Chem.  2006,  71:  3198 
  • 15 Watson DA. Fan X. Buchwald SL. J. Org. Chem.  2008,  73:  7096 
  • 16 Urano T. Kitamura A. Sakuragi H. Tokumaru K. Chem. Lett.  1983,  867 
  • 17 Endo T. Saotome Y. Okawara M. J. Am. Chem. Soc.  1984,  106:  1124 
  • 18 Shintou T. Fukumoto K. Mukaiyama T. Bull. Chem. Soc. Jpn.  2004,  77:  1569 
  • 19 Chan W.-C. Mooney JA. Windle AH. Mol. Cryst. Liq. Cryst.  1989,  174:  75 
  • 20 Silverman SK. Foote CS. J. Am. Chem. Soc.  1991,  113:  7672 
  • 21 Chen CT. Munot YS. J. Org. Chem.  2005,  70:  8625 
  • 22 Ishihara K. Kubota M. Kurihara H. Yamamoto H. J. Org. Chem.  1996,  61:  4560 
  • 23 Doering WE. Levy LK. J. Am. Chem. Soc.  1955,  77:  509 
  • 24 Kanoh S. Nishimura T. Naka M. Motoi M. Tetrahedron  2002,  58:  7065 
  • 25 Yamazaki S. Org. Lett.  1999,  1:  212 
8

The additive Et4NCl was sometimes effective in the carbamoylation of aryl halides. See ref. 6.