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Synthesis 2010(24): 4154-4168  
DOI: 10.1055/s-0030-1258322
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Coupling Reaction of α-Diazocarbonyl Compounds with Aromatic Boronic Acids or Halides

Cheng Peng, Guobin Yan, Yan Wang, Yubo Jiang, Yan Zhang, Jianbo Wang*
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China
Fax: +86(10)62751708; e-Mail: wangjb@pku.edu.cn;
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Publication History

Received 6 September 2010
Publication Date:
15 November 2010 (online)

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Abstract

Efficient palladium-catalyzed cross-coupling reactions of α-diazocarbonyl compounds and arylboronic acids or aryl halides have been developed. The reaction proceeds smoothly for a range of diazo compounds, boronic acids, and halides. The coupling reaction conditions tolerate various substituents on the aromatic rings of the substrates, such as chloro, fluoro, acyl, oxo, ester, and nitro groups. This coupling reaction constitutes a novel access to α-aryl-substituted α,β-unsaturated carbonyl compounds. Mechanistically, palladium-carbene is supposed to be the key intermediate; its formation is followed by migratory insertion of an aryl group to the carbenic carbon of the palladium-carbene complex and subsequent β-hydride elimination. Kinetic isotope effect (KIE) data measured for intra- and intermolecular competition experiments suggest that β-hydride elimination is not involved in the rate-determining step.

Key words

palladium catalysis - cross-coupling - diazo compounds - aryl halides - arylboronic acids

    References

  • For selected comprehensive reviews, see:
  • 1a Ye T. McKervey MA. Chem. Rev.  1994,  94:  1091 
    Search in Google Scholar
  • 1b Doyle MP. McKervey MA. Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds   Wiley-Interscience; New York: 1998. 
  • 1c Zhang Z. Wang J. Tetrahedron  2008,  64:  6577 
    Search in Google Scholar
  • For examples of diazo-compound reactions catalyzed by transition-metal complexes other than rhodium(II) or copper(I) complexes, see the following references. For ruthenium-complex-catalyzed reactions, see:
  • 2a Bonaccorsi C. Mezzetti A. Organometallics  2005,  24:  4953 
    Search in Google Scholar
  • 2b Wang M.-Z. Xu H.-W. Liu Y. Wong M.-K. Che C.-M. Adv. Synth. Catal.  2006,  348:  2391 
    Search in Google Scholar
  • 2c Bonaccorsi C. Santoro F. Gischig S. Mezzetti A. Organometallics  2006,  25:  2002 
    Search in Google Scholar
  • 2d Xiao Q. Wang J. Acta Chim. Sin.  2007,  65:  1733 
    Search in Google Scholar
  • For cobalt-complex-catalyzed reactions, see:
  • 2e Chen Y. Zhang XP. J. Org. Chem.  2004,  69:  2431 
    Search in Google Scholar
  • 2f Chen Y. Fields KB. Zhang XP. J. Am. Chem. Soc.  2004,  126:  14718 
    Search in Google Scholar
  • For chromium-complex-catalyzed reactions, see:
  • 2g Hahn ND. Nieger M. Dötz KH. Eur. J. Org. Chem.  2004,  1049 
  • For iron-complex-catalyzed reactions, see:
  • 2h Li Y. Huang J.-S. Zhou Z.-Y. Che C.-M. You X.-Z. J. Am. Chem. Soc.  2002,  124:  13185 
    Search in Google Scholar
  • 2i Du G. Andrioletti B. Rose E. Woo LK. Organometallics  2002,  21:  4490 
    Search in Google Scholar
  • 2j Edulji SK. Nguyen ST. Organometallics  2003,  22:  3374 
    Search in Google Scholar
  • 2k Aviv I. Gross Z. Chem. Commun.  2006,  4477 
  • For silver-complex-catalyzed reactions, see:
  • 2l Dias HVR. Browning RG. Polach SA. Diyabalanage HVK. Lovely CJ. J. Am. Chem. Soc.  2003,  125:  9270 
    Search in Google Scholar
  • 2m Thompson JL. Davies HML. J. Am. Chem. Soc.  2007,  129:  6090 
    Search in Google Scholar
  • For gold-complex-catalyzed reactions, see:
  • 2n Fructos MR. Belderrain TR. Frémont P. Scott NM. Nolan SP. Díaz-Requejo MM. Pérez PJ. Angew. Chem. Int. Ed.  2005,  44:  5284 
    Search in Google Scholar
  • For reviews, see:
  • 3a Negishi E.-i. Handbook of Organopalladium Chemistry for Organic Synthesis   Wiley-Interscience; New York: 2002. 
  • 3b Tsuji J. Palladium Reagents and Catalysts. New Perspectives for the 21st Century   2nd ed.:  Wiley; Chichester: 2004. 
    Search in Google Scholar
  • 3c de Meijere A. Diederich F. Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  Wiley-VCH; Weinheim: 2004. 
    Search in Google Scholar
  • 3d King AO. Yasuda N. Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Pharmaceuticals, In Topics in Organometallic Chemistry   Vol. 6:  Springer; New York: 2004.  p.205-245  
    Search in Google Scholar
  • For the most recent reviews, see:
  • 4a Cacchi S. Fabrizi G. Chem. Rev.  2005,  105:  2873 
    Search in Google Scholar
  • 4b Christmann U. Vilar R. Angew. Chem. Int. Ed.  2005,  44:  366 
    Search in Google Scholar
  • 4c Rollet P. Kleist W. Dufaud V. Djakovitch L. J. Mol. Catal.  2005,  241:  39 
    Search in Google Scholar
  • 4d Zapf A. Beller M. Chem. Commun.  2005,  431 
  • 4e Frisch A. Beller M. Angew. Chem. Int. Ed.  2005,  44:  674 
    Search in Google Scholar
  • 4f Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4442 
    Search in Google Scholar
  • 4g Campeau L.-C. Fagnou K. Chem. Commun.  2006,  1253 
  • 4h Roglans A. Pla-Quintana A. Moreno-Mañas M. Chem. Rev.  2006,  106:  4622 
    Search in Google Scholar
  • 4i Reiser O. Angew. Chem. Int. Ed.  2006,  45:  2838 
    Search in Google Scholar
  • 4j Liebscher J. Yin L. Chem. Rev.  2007,  107:  133 
    Search in Google Scholar
  • 4k Doucet H. Hierso J.-C. Angew. Chem. Int. Ed.  2007,  46:  834 
    Search in Google Scholar
  • 4l Surry DS. Buchwald SL. Angew. Chem. Int. Ed.  2008,  47:  6338 
    Search in Google Scholar
  • 4m Alonso F. Beletskaya IP. Yus M. Tetrahedron  2008,  64:  3047 
    Search in Google Scholar
  • For studies on stable palladium-carbene species, see:
  • 5a Albéniz AC. Espinet P. Manrique R. Pérez-Mateo A. Angew. Chem. Int. Ed.  2002,  41:  2363 
    Search in Google Scholar
  • 5b Bröring M. Brandt CD. Stellwag S. Chem. Commun.  2003,  2344 
  • 5c Danopoulos AA. Tsoureas N. Green JC. Hursthouse MB. Chem. Commun.  2003,  756 
  • 5d Solé D. Vallverdú L. Solans X. Font-Bardia M. Bonjoch J. Organometallics  2004,  23:  1438 
    Search in Google Scholar
  • 5e Albéniz AC. Espinet P. Manrique R. Pérez-Mateo A. Chem. Eur. J.  2005,  11:  1565 
    Search in Google Scholar
  • 5f Albéniz AC. Espinet P. Pérez-Mateo A. Nova A. Ujaque G. Organometallics  2006,  25:  1293 
    Search in Google Scholar
  • 5g López-Alberca MP. Mancheño MJ. Fernández I. Gómez-Gallego M. Sierra MA. Torres R. Org. Lett.  2007,  9:  1757 
    Search in Google Scholar
  • For examples, see:
  • 6a Trost BM. Tanoury GJ. J. Am. Chem. Soc.  1988,  110:  1636 
    Search in Google Scholar
  • 6b Trost BM. Hashmi ASK. Angew. Chem. Int. Ed.  1993,  32:  1085 
    Search in Google Scholar
  • 6c Schweizer S. Song Z.-Z. Meyer FE. Parsons PJ. de Meijere A. Angew. Chem. Int. Ed.  1999,  38:  1452 
    Search in Google Scholar
  • 6d Miki K. Nishino F. Ohe K. Uemura S. J. Am. Chem. Soc.  2002,  124:  5260 
    Search in Google Scholar
  • 6e Nakamura I. Bajracharya GB. Mizushima Y. Yamamoto Y. Angew. Chem. Int. Ed.  2002,  41:  4328 
    Search in Google Scholar
  • 6f Fillion E. Taylor NJ. J. Am. Chem. Soc.  2003,  125:  12700 
    Search in Google Scholar
  • 6g Ohno H. Takeoka Y. Miyamura K. Kadoh Y. Tanaka T. Org. Lett.  2003,  5:  4763 
    Search in Google Scholar
  • 6h Gömez-Gallego M. Mancheño MJ. Sierra MA. Acc. Chem. Res.  2005,  38:  44 
    Search in Google Scholar
  • 6i Trépanier V. Fillion E. Organometallics  2007,  26:  30 
    Search in Google Scholar
  • 6j Shi M. Liu L.-P. Tang J. J. Am. Chem. Soc.  2006,  128:  7430 
    Search in Google Scholar
  • 7a Herrmann WA. Kocker C. Angew. Chem. Int. Ed.  1997,  36:  2162 
    Search in Google Scholar
  • 7b Herrmann WA. Angew. Chem. Int. Ed.  2002,  41:  1290 
    Search in Google Scholar
  • 7c Viciu MS. Nolan SP. Top. Organomet. Chem.  2005,  14:  241 
    Search in Google Scholar
  • 7d Marion N. Nolan SP. Acc. Chem. Res.  2008,  41:  1440 
    Search in Google Scholar
  • 8 For a review on the cyclopropanation of palladium-carbenes, see: Reiser O. In Handbook of Organopalladium Chemistry for Organic Synthesis   Vol. 1:  Negishi E.-i. Wiley; New York: 2002.  p.1561-1577  
    Search in Google Scholar
  • 9a Doyle MP. Chem. Rev.  1986,  86:  919 
    Search in Google Scholar
  • 9b Anciaux AJ. Hubert AJ. Noels AF. Petiniot N. Teyssié P.
    J. Org. Chem.  1980,  45:  695 
    Search in Google Scholar
  • 10a Ihara E. Haida N. Iio M. Inoue K. Macromolecules  2003,  36:  36 
    Search in Google Scholar
  • 10b Ihara E. Fujioka M. Haida N. Itoh T. Inoue K. Macromolecules  2005,  38:  2101 
    Search in Google Scholar
  • 10c Ihara E. Nakada A. Itoh T. Inoue K. Macromolecules  2006,  39:  6440 
    Search in Google Scholar
  • 10d Ihara E. Kida M. Fujioka M. Haida N. Itoh T. Inoue K. J. Polym. Sci.: Part A: Polym. Chem.  2007,  45:  1536 
    Search in Google Scholar
  • 11 Chen S. Ma J. Wang J. Tetrahedron Lett.  2008,  49:  6781 
    CrossrefSearch in Google Scholar
  • 12a Greenman KL. Carter DS. Van Vranken DL. Tetrahedron  2001,  57:  5219 
    Search in Google Scholar
  • 12b Greenman KL. Van Vranken DL. Tetrahedron  2005,  61:  6438 
    Search in Google Scholar
  • 12c Devine SKJ. Van Vranken DL. Org. Lett.  2007,  9:  2047 
    Search in Google Scholar
  • 12d Barluenga J. Moriel P. Valdés C. Aznar F. Angew. Chem. Int. Ed.  2007,  46:  5587 
    Search in Google Scholar
  • 12e Barluenga J. Tomás-Gamasa M. Moriel P. Aznar F. Valdés C. Chem. Eur. J.  2008,  14:  4792 
    Search in Google Scholar
  • 12f Peng C. Wang Y. Wang J.
    J. Am. Chem. Soc.  2008,  130:  1566 
    Search in Google Scholar
  • 12g Chen S. Wang J. Chem. Commun.  2008,  4198 
  • 12h Devine SKJ. Van Vranken DL. Org. Lett.  2008,  10:  1909 
    Search in Google Scholar
  • 12i Kudirka R. Van Vranken DL. J. Org. Chem.  2008,  73:  3585 
    Search in Google Scholar
  • 12j Yu W.-Y. Tsoi Y.-T. Zhou Z. Chan ASC. Org. Lett.  2009,  11:  469 
    Search in Google Scholar
  • 12k Xiao Q. Ma J. Yang Y. Zhang Y. Wang J. Org. Lett.  2009,  11:  4732 
    Search in Google Scholar
  • 12l Kudirka R. Devine SKJ. Adams CS. Van Vranken DL. Angew. Chem. Int. Ed.  2009,  48:  3677 
    Search in Google Scholar
  • 12m Zhang Z. Liu Y. Gong M. Zhao X. Zhang Y. Wang J. Angew. Chem. Int. Ed.  2010,  49:  1139 
    Search in Google Scholar
  • 12n Zhao X. Jing J. Lu K. Zhang Y. Wang J. Chem. Commun.  2010,  46:  1724 
    Search in Google Scholar
  • 13a Suzuki A. Acc. Chem. Res.  1982,  15:  178 
    Search in Google Scholar
  • 13b Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Search in Google Scholar
  • For direct reaction of diazo compounds with boronic acids or their derivatives, see:
  • 14a Peng C. Zhang W. Yan G. Wang J. Org. Lett.  2009,  11:  1667 
    Search in Google Scholar
  • 14b Barluenga J. Tomás-Gamasa M. Aznar F. Valdés C. Nat. Chem.  2009,  1:  433 
    Search in Google Scholar
  • 15a Huang X. Anderson KW. Zim D. Jiang L. Klapars A. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  6653 
    Search in Google Scholar
  • 15b Nguyen HN. Huang X. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  11818 
    Search in Google Scholar
  • For examples, see:
  • 16a Du X. Suguro M. Hirabayashi K. Mori A. Org. Lett.  2001,  3:  3313 
    Search in Google Scholar
  • 16b Enquist P.-A. Lindh J. Nilsson P. Larhed M. Green Chem.  2006,  8:  338 
    Search in Google Scholar
  • 16c Yoo KS. Yoon CH. Jung KW. J. Am. Chem. Soc.  2006,  128:  16384 
    Search in Google Scholar
  • For selected reviews on palladium-catalyzed carbonylations, see:
  • 17a Colquhoun HM. Thompson DJ. Twigg MV. Carbonylation. Direct Synthesis of Carbonyl Compounds   Plenum; New York: 1991. 
  • 17b Handbook of Organopalladium Chemistry for Organic Synthesis   Negishi E.-i. Wiley; New York: 2002.  Chap. VI. p.2505-2714  
  • 17c Barnard CFJ. Organometallics  2008,  27:  5402 
    Search in Google Scholar
  • 17d Brennführer A. Neumann H. Beller M. Angew. Chem. Int. Ed.  2009,  48:  4114 
    Search in Google Scholar
  • 17e Brennführer A. Neumann H. Beller M. ChemCatChem  2009,  1:  28 
    Search in Google Scholar
  • 17f Grigg R. Mutton SP. Tetrahedron  2010,  66:  5515 
    Search in Google Scholar
  • It has been reported that syn-β-hydride elimination has a substantial kinetic isotope effect (KIE, typical values of k H/k D = 2-3). For examples, see:
  • 18a Keinan E. Kumar S. Dangur V. Vaya J. J. Am. Chem. Soc.  1994,  116:  11151 
    Search in Google Scholar
  • 18b Netherton MR. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  3910 
    Search in Google Scholar
  • The value of KIE for anti-β-hydride elimination is higher (k H/k D = 5-7); see:
  • 18c Chrisope DR. Beak P. Saunders WH. J. Am. Chem. Soc.  1988,  110:  230 
    Search in Google Scholar
  • 18d Takacs JM. Lawson EC. Clement F. J. Am. Chem. Soc.  1997,  119:  5956 
    Search in Google Scholar
  • 19 Levin JI. Tetrahedron Lett.  1993,  34:  6211 
    CrossrefSearch in Google Scholar
  • 20 Silveira PB. Monteiro AL. J. Mol. Catal. A: Chem.  2006,  247:  1 
    CrossrefSearch in Google Scholar
  • 21 Nishimura K. Ono M. Nagaoka Y. Tomioka K. Angew. Chem. Int. Ed.  2001,  40:  440 
    CrossrefSearch in Google Scholar
  • 22 Berthiol F. Doucet H. Santelli M. Eur. J. Org. Chem.  2003,  1091 
    Crossref
  • 23 Gerster M, Maeder D, and Rotzinger B. inventors; PCT Int. Appl. WO  2006024611.  ; Chem. Abstr. 2006, 333233
  • 24 Selva M. Tundo P. J. Org. Chem.  2006,  71:  1464 
    CrossrefPubMedSearch in Google Scholar
  • 25 Jefford CW. Bernardinelli G. Wang Y. Spellmeyer DC. Buda A. Houk KN. J. Am. Chem. Soc.  1992,  114:  1157 
    CrossrefSearch in Google Scholar
  • 26 Chang MY. Chen ST. Chang NC. Tetrahedron  2002,  58:  3623 
    CrossrefSearch in Google Scholar
  • 27 Zhang C. Ito H. Maeda Y. Shirai N. Ikeda S. Sato Y. J. Org. Chem.  1999,  64:  581 
    CrossrefSearch in Google Scholar
  • 28 Reger DL. Mintz E. Lebioda L. J. Am. Chem. Soc.  1986,  108:  1940 
    CrossrefSearch in Google Scholar
  • 29 Jacobi PA. Brielmann HL. Cann RO. J. Org. Chem.  1994,  59:  5305 
    CrossrefSearch in Google Scholar
  • 30 Hon YS. Hsu TR. Chen CY. Lin YH. Chang FJ. Hsieh CH. Szu PH. Tetrahedron  2003,  59:  1509 
    CrossrefSearch in Google Scholar
  • 31 Felpin F.-X. J. Org. Chem.  2005,  70:  8575 
    CrossrefPubMedSearch in Google Scholar