PDF herunterladen
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;
Weitere Informationen

Publikationsverlauf

Received 27 July 2009
Publikationsdatum:
23. Oktober 2009 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik

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. 
  • 1b Beller M. Bolm C. Transition Metals for Organic Synthesis, Building Blocks and Fine Chemicals   2nd ed., Vol. 1-2:  Wiley-VCH; Weinheim: 2004. 
    Suche in Google Scholar
  • 1c Handbook of Organopalladium for Organic Synthesis   Vol. 1-2:  Nigeshi E. Wiley-Interscience; New York: 2002. 
  • 1d Tsuji J. Palladium Reagents and Catalysts   2nd ed.:  Wiley; Chichester: 2004. 
    Suche in Google Scholar
  • 1e Yin LX. Liebscher J. Chem. Rev.  2007,  107:  133 
    Suche in Google Scholar
  • 1f Corbet J.-P. Mignani G. Chem. Rev.  2006,  106:  2651 
    Suche in Google Scholar
  • 1g Roglans A. Pla-Quintana A. Moreno-Mañas M. Chem. Rev.  2006,  106:  4622 
    Suche in Google Scholar
  • 1h Molander GA. Ellis N. Acc. Chem. Res.  2007,  40:  275 
    Suche in Google Scholar
  • For recent reviews on ligand developments, see:
  • 2a Surry DS. Buchwald SL. Angew. Chem. Int. Ed.  2008,  47:  6338 
    Suche in Google Scholar
  • 2b Martin R. Buchwald SL. Acc. Chem. Res.  2008,  41:  1461 
    Suche in Google Scholar
  • 2c Hartwig JF. Acc. Chem. Res.  2008,  41:  1534 
    Suche in Google Scholar
  • 2d Kwong FY. Chan ASC. Synlett  2008,  1440 
  • 3 For a pertinent review on aryl chloride couplings, see: Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Suche in Google Scholar
  • 4 Tobisu M. Shimasaki T. Chatani N. Angew. Chem. Int. Ed.  2008,  47:  4866 
    CrossrefSuche in Google Scholar
  • 5 Darses S. Jeffery T. Genet J.-P. Brayer J.-L. Demoute J.-P. Tetrahedron Lett.  1996,  37:  3857 
    CrossrefSuche in Google Scholar
  • 6a Dabbaka SR. Vogel P. J. Am. Chem. Soc.  2003,  125:  15292 
    Suche in Google Scholar
  • 6b Dabbaka SR. Vogel P. Org. Lett.  2004,  6:  95 
    Suche in 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 
    Suche in Google Scholar
  • 7b So CM. Lau CP. Chan ASC. Kwong FY. J. Org. Chem.  2008,  73:  7734 
    Suche in Google Scholar
  • 7c Zhang L. Meng T. Wu J. J. Org. Chem.  2007,  72:  9346 
    Suche in Google Scholar
  • 7d Roy AH. Hartwig JF. J. Am. Chem. Soc.  2003,  125:  8704 
    Suche in Google Scholar
  • 7e Limmert ME. Roy AH. Hartwig JF. J. Org. Chem.  2005,  70:  9364 
    Suche in Google Scholar
  • 7f Ackermann L. Althammer A. Org. Lett.  2006,  8:  3457 
    Suche in Google Scholar
  • 7g Hansen AL. Ebran J.-P. Ahlquist M. Norrby P.-O. Skrydstrup T. Angew. Chem. Int. Ed.  2006,  45:  3349 
    Suche in 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 
    Suche in Google Scholar
  • 7i Tang ZY. Hu QS. J. Am. Chem. Soc.  2004,  126:  3058 
    Suche in Google Scholar
  • 7j Percec V. Golding GM. Smidrkal J. Weichold O. J. Org. Chem.  2004,  69:  3447 
    Suche in 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 
    Suche in Google Scholar
  • 8b So CM. Lau CP. Kwong FY. Angew. Chem. Int. Ed.  2008,  47:  8059 
    Suche in Google Scholar
  • 8c So CM. Lee HW. Lau CP. Kwong FY. Org. Lett.  2009,  11:  317 
    Suche in Google Scholar
  • 8d Fors BP. Watson DA. Biscoe MR. Buchwald SL. J. Am. Chem. Soc.  2008,  130:  13552 
    Suche in Google Scholar
  • 8e Zhang L. Qing J. Yang P. Wu J. Org. Lett.  2008,  10:  4971 
    Suche in Google Scholar
  • For Ni-catalyzed ArOMs couplings, see:
  • 8f Percec V. Bae J.-Y. Hill DH. J. Org. Chem.  1995,  60:  1060 
    Suche in Google Scholar
  • 8g Percec V. Bae J.-Y. Hill DH. J. Org. Chem.  1995,  60:  1066 
    Suche in Google Scholar
  • 8h Ueda M. Saitoh A. Oh-tani S. Miyaura N. Tetrahedron  1998,  54:  13079 
    Suche in Google Scholar
  • 9a Guan B.-T. Wang Y. Li B.-J. Yu D.-G. Shi Z.-J. J. Am. Chem. Soc.  2008,  130:  14468 
    Suche in Google Scholar
  • 9b Quasdorf KW. Tian X. Garg NK. J. Am. Chem. Soc.  2008,  130:  14422 
    Suche in 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 
    Suche in Google Scholar
  • For a related decarboxylative coupling, see:
  • 9d Gooßen LJ. Deng G. Levy LM. Science  2006,  313:  662 
    Suche in 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 
  • 10b Matsuura Y. Tamura M. Kochi T. Sato M. Chatani N. Kakiuchi F. J. Am. Chem. Soc.  2007,  129:  9858 
    Suche in Google Scholar
  • 11a Valle LD. Stille JK. Hegedus LS. J. Org. Chem.  1990,  55:  3019 
    Suche in Google Scholar
  • 11b Uozumi Y. Danjo H. Hayashi T.
    J. Org. Chem.  1999,  64:  3384 
    Suche in Google Scholar
  • 11c Bouyssi D. Gerusz V. Balme G. Eur. J. Org. Chem.  2002,  2445 
  • 11d Kuwano R. Yokogi M. Chem. Commun.  2005,  5899 
  • For our recent developments on indolyl phosphine ligands, see:
  • 12a So CM. Yeung CC. Lau CP. Kwong FY.
    J. Org. Chem.  2008,  73:  7803 
    Suche in 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
  • 13 So CM. Lau CP. Kwong FY. Org. Lett.  2007,  9:  2795 
    CrossrefSuche in Google 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 
    Crossref
  • 16a Komiya S. Suzuki J.-I. Miki K. Kasai N. Chem. Lett.  1987,  16:  1287 
    Suche in Google Scholar
  • 16b Planas JG. Marumo T. Ichikawa Y. Hirano M. Komiya S. J. Chem. Soc., Dalton Trans.  2000,  2613 
  • 17 Yu J.-Y. Kuwano R. Angew. Chem. Int. Ed.  2009,  DOI: 101002/anie. 200903146 
15

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