Download PDF
Synlett 2009(19): 3151-3154  
DOI: 10.1055/s-0029-1218283
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Cross-Coupling of Arylboronic Acids Using Vinyl Acetate as the Electrophilic Partner

Hang Wai Lee, Fuk Yee Kwong*
Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong, P. R. of China
Fax: +85223649932; e-Mail: bcfyk@inet.polyu.edu.hk;
Further Information

Publication History

Received 27 July 2009
Publication Date:
23 October 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

The first Suzuki-type cross-coupling between arylboronic acids and vinyl acetate is disclosed. The acetoxy moiety as the leaving group is realized in the coupling process. Rhodium complexes were found to be highly effective for promoting this transformation. In contrast, the present well-known nickel and palladium complexes were inferior for this catalysis when vinyl acetate was used as the electrophilic partner.

Key words

cross-coupling - catalysis - rhodium - vinyl acetate

    References and Notes

  • 1a Metal-Catalyzed Cross-Coupling Reactions   2nd ed., Vol. 1-2:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 1b Beller M. Bolm C. Transition Metals for Organic Synthesis, Building Blocks and Fine Chemicals   2nd ed., Vol. 1-2:  Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 1c Handbook of Organopalladium for Organic Synthesis   Vol. 1-2:  Nigeshi E. Wiley-Interscience; New York: 2002. 
    Google Scholar
  • 1d Tsuji J. Palladium Reagents and Catalysts   2nd ed.:  Wiley; Chichester: 2004. 
    Google Scholar
  • 1e Yin LX. Liebscher J. Chem. Rev.  2007,  107:  133 
    Google Scholar
  • 1f Corbet J.-P. Mignani G. Chem. Rev.  2006,  106:  2651 
    Google Scholar
  • 1g Roglans A. Pla-Quintana A. Moreno-Mañas M. Chem. Rev.  2006,  106:  4622 
    Google Scholar
  • 1h Molander GA. Ellis N. Acc. Chem. Res.  2007,  40:  275 
    Google Scholar
  • For recent reviews on ligand developments, see:
  • 2a Surry DS. Buchwald SL. Angew. Chem. Int. Ed.  2008,  47:  6338 
    Google Scholar
  • 2b Martin R. Buchwald SL. Acc. Chem. Res.  2008,  41:  1461 
    Google Scholar
  • 2c Hartwig JF. Acc. Chem. Res.  2008,  41:  1534 
    Google Scholar
  • 2d Kwong FY. Chan ASC. Synlett  2008,  1440 
    Google Scholar
  • 3 For a pertinent review on aryl chloride couplings, see: Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Google Scholar
  • 4 Tobisu M. Shimasaki T. Chatani N. Angew. Chem. Int. Ed.  2008,  47:  4866 
    CrossrefGoogle Scholar
  • 5 Darses S. Jeffery T. Genet J.-P. Brayer J.-L. Demoute J.-P. Tetrahedron Lett.  1996,  37:  3857 
    CrossrefGoogle Scholar
  • 6a Dabbaka SR. Vogel P. J. Am. Chem. Soc.  2003,  125:  15292 
    Google Scholar
  • 6b Dabbaka SR. Vogel P. Org. Lett.  2004,  6:  95 
    Google Scholar
  • For ArOTs in Pd-catalyzed C-C bond couplings, see:
  • 7a Nguyen HN. Huang X. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  11818 
    Google Scholar
  • 7b So CM. Lau CP. Chan ASC. Kwong FY. J. Org. Chem.  2008,  73:  7734 
    Google Scholar
  • 7c Zhang L. Meng T. Wu J. J. Org. Chem.  2007,  72:  9346 
    Google Scholar
  • 7d Roy AH. Hartwig JF. J. Am. Chem. Soc.  2003,  125:  8704 
    Google Scholar
  • 7e Limmert ME. Roy AH. Hartwig JF. J. Org. Chem.  2005,  70:  9364 
    Google Scholar
  • 7f Ackermann L. Althammer A. Org. Lett.  2006,  8:  3457 
    Google Scholar
  • 7g Hansen AL. Ebran J.-P. Ahlquist M. Norrby P.-O. Skrydstrup T. Angew. Chem. Int. Ed.  2006,  45:  3349 
    Google Scholar
  • For Ni-catalyzed C-C couplings of ArOTs, see:
  • 7h Zim D. Lando VR. Dupont J. Monteiro AL. Org. Lett.  2001,  3:  3049 
    Google Scholar
  • 7i Tang ZY. Hu QS. J. Am. Chem. Soc.  2004,  126:  3058 
    Google Scholar
  • 7j Percec V. Golding GM. Smidrkal J. Weichold O. J. Org. Chem.  2004,  69:  3447 
    Google Scholar
  • For ArOMs in Pd-catalyzed couplings, see:
  • 8a So CM. Zhou Z. Lau CP. Kwong FY. Angew. Chem. Int. Ed.  2008,  47:  6402 
    Google Scholar
  • 8b So CM. Lau CP. Kwong FY. Angew. Chem. Int. Ed.  2008,  47:  8059 
    Google Scholar
  • 8c So CM. Lee HW. Lau CP. Kwong FY. Org. Lett.  2009,  11:  317 
    Google Scholar
  • 8d Fors BP. Watson DA. Biscoe MR. Buchwald SL. J. Am. Chem. Soc.  2008,  130:  13552 
    Google Scholar
  • 8e Zhang L. Qing J. Yang P. Wu J. Org. Lett.  2008,  10:  4971 
    Google Scholar
  • For Ni-catalyzed ArOMs couplings, see:
  • 8f Percec V. Bae J.-Y. Hill DH. J. Org. Chem.  1995,  60:  1060 
    Google Scholar
  • 8g Percec V. Bae J.-Y. Hill DH. J. Org. Chem.  1995,  60:  1066 
    Google Scholar
  • 8h Ueda M. Saitoh A. Oh-tani S. Miyaura N. Tetrahedron  1998,  54:  13079 
    Google Scholar
  • 9a Guan B.-T. Wang Y. Li B.-J. Yu D.-G. Shi Z.-J. J. Am. Chem. Soc.  2008,  130:  14468 
    Google Scholar
  • 9b Quasdorf KW. Tian X. Garg NK. J. Am. Chem. Soc.  2008,  130:  14422 
    Google Scholar
  • 9c Li B.-J. Li Y.-Z. Lu X.-Y. Liu J. Guan B.-T. Shi Z.-J. Angew. Chem. Int. Ed.  2008,  47:  10124 
    Google Scholar
  • For a related decarboxylative coupling, see:
  • 9d Gooßen LJ. Deng G. Levy LM. Science  2006,  313:  662 
    Google Scholar
  • To our knowledge, there is no literature report on cross-coupling of vinyl acetate before. Only oxidative coupling and 2-phenylpyridine C-H activation/coupling were reported, see:
  • 10a Amatore M. Gosmini C. Périchon J. Eur. J. Org. Chem.  2005,  989 
    Google Scholar
  • 10b Matsuura Y. Tamura M. Kochi T. Sato M. Chatani N. Kakiuchi F. J. Am. Chem. Soc.  2007,  129:  9858 
    Google Scholar
  • 11a Valle LD. Stille JK. Hegedus LS. J. Org. Chem.  1990,  55:  3019 
    Google Scholar
  • 11b Uozumi Y. Danjo H. Hayashi T.
    J. Org. Chem.  1999,  64:  3384 
    Google Scholar
  • 11c Bouyssi D. Gerusz V. Balme G. Eur. J. Org. Chem.  2002,  2445 
    Google Scholar
  • 11d Kuwano R. Yokogi M. Chem. Commun.  2005,  5899 
    Google Scholar
  • For our recent developments on indolyl phosphine ligands, see:
  • 12a So CM. Yeung CC. Lau CP. Kwong FY.
    J. Org. Chem.  2008,  73:  7803 
    Google Scholar
  • 12b Lee HW. Lam FL. So CM. Lau CP. Chan ASC. Kwong FY. Angew. Chem. Int. Ed.  2009,  48  ; DOI: 10.1002/anie.200904033
    Google Scholar
  • 13 So CM. Lau CP. Kwong FY. Org. Lett.  2007,  9:  2795 
    CrossrefGoogle Scholar
  • 14 We have attempted to use MW reactor instead of conventional heating to perform this reaction. Under the same reaction conditions except MW heating at 130 ˚C for 1 h, only 25% yield of p-tert-butylstyrene was obtained. For our recent reference on rhodium catalysis under MW conditions, see: Lee HW. Lee LN. Chan ASC. Kwong FY. Eur. J. Org. Chem.  2008,  3403 
    CrossrefGoogle Scholar
  • 16a Komiya S. Suzuki J.-I. Miki K. Kasai N. Chem. Lett.  1987,  16:  1287 
    Google Scholar
  • 16b Planas JG. Marumo T. Ichikawa Y. Hirano M. Komiya S. J. Chem. Soc., Dalton Trans.  2000,  2613 
    Google Scholar
  • 17 Yu J.-Y. Kuwano R. Angew. Chem. Int. Ed.  2009,  DOI: 101002/anie. 200903146 
    Google Scholar
15

We tried to lower the loading of vinyl acetate to 2 equiv (with respected to arylboronic acid). However, the product yield dropped significantly.