Synthesis 2012; 44(12): 1885-1891
DOI: 10.1055/s-0031-1290943
special topic
© Georg Thieme Verlag Stuttgart · New York

Tandem Decarboxylative Allylation and Fragmentation of Allyl Benzocyclobutenyl Carbonates: Access to ortho-Functionalized Aryls from Aryl Bromides

David Rosa
Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada, Fax: +1(416)7365936   Email: aorellan@yorku.ca
,
Andrei Chtchemelinine
Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada, Fax: +1(416)7365936   Email: aorellan@yorku.ca
,
Arturo Orellana*
Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada, Fax: +1(416)7365936   Email: aorellan@yorku.ca
› Author Affiliations
Further Information

Publication History

Received: 19 March 2012

Accepted: 22 March 2012

Publication Date:
08 May 2012 (eFirst)

Abstract

Allyl benzocyclobutyl carbonates yield ortho-allyl α-aryl ketones through a palladium-catalyzed decarboxylative allylation, fragmentation, and cross-coupling process.

Supporting Information

 
  • References

    • For recent reviews on transition-metal-catalyzed β-carbo-elimination reactions see:

    • 1a Seiser T, Saget T, Tran DC, Cramer N. Angew. Chem. Int. Ed. 2011; 50: 5540
    • 1b Murakami M, Matsuda T. Chem. Commun. 2011; 47: 1100
    • 1c Aïssa C. Synthesis 2011; 3389
    • 1d Seiser T, Cramer N. Org. Biomol. Chem. 2009; 7: 2835
    • 1e Satoh T, Miura M. Top. Organomet. Chem. 2007; 24: 61
    • 1f Murakami M, Makino M, Ashida S, Matsuda T. Bull. Chem. Soc. Jpn. 2006; 79: 1315
    • 1g Satoh T, Miura M. Top. Organomet. Chem. 2005; 14: 1
    • 1h Nishimura T, Uemura S. Synlett 2004; 201
    • 1i Kuwajima I, Nakamura E In Comprehensive Organic Synthesis . Vol. 2. Trost B, Fleming I. Pergamon; Oxford: 1991: 441
    • 1j Kuwajima I, Nakamura I. Top. Curr. Chem. 1990; 155: 1
    • 1k Kuwajima I. Pure Appl. Chem. 1988; 60: 115
    • 2a Rosa D, Orellana A. Chem. Commun. 2012; 48: 1922
    • 2b Rosa D, Orellana A. Org. Lett. 2011; 13: 110
  • 3 Rosa D, Chtchemelinine A, Orellana A. J. Org. Chem. 2011; 76: 9157
  • 4 Recent review: Weaver JD, Recio A, Grenning AJ, Tunge JA. Chem. Rev. 2011; 111: 1846
  • 5 The base-catalyzed cleavage of benzocyclobutenols is generally not selective. Seminal report: Cava MP, Muth K. J. Am. Chem. Soc. 1960; 82: 652
  • 6 For a related process see: Schulz SR, Blechert S. Angew. Chem. Int. Ed. 2007; 46: 3966
  • 7 This functional group disposition is found in some natural products. Shirataki Y, Yoshida S, Sugita Y, Yokoe I, Komatsu M, Ohyama M, Tanaka T, Iinuma M. Phytochemistry 1997; 44: 715
    • For selected examples of benzocyclobutenol synthesis, see:

    • 8a Photochemical synthesis: Ito Y, Takahashi H, Hasegawa J.-Y, Turro NJ. Tetrahedron 2009; 65: 677
    • 8b Intramolecular reaction of o-acylbenzyllithiums: Kobayashi K, Kawakita M, Uchida M, Nishimura K, Mannami T, Irisawa S, Morikawa O, Konishi H. J. Org. Chem. 1999; 64: 3557
    • 8c Intramolecular addition of aryllithiums to ketones: Aidhen IS, Narasimhan NS. Tetrahedron Lett. 1991; 32: 2171
    • 8d Pb(OAc)4-mediated decarboxylation of the corresponding carboxylic acids: Macdonald DI, Durst T. Tetrahedron Lett. 1986; 27: 2235
    • 8e Metalation of o-halostyrene oxides: Akguen E, Glinski MB, Dhawan KL, Durst T. J. Org. Chem. 1981; 46: 2730
    • Selected examples:

    • 9a Tambar UK, Ebner DC, Stoltz B. J. Am. Chem. Soc. 2006; 128: 11752
    • 9b Macdonald DI, Durst T. J. Org. Chem. 1988; 53: 3663
  • 10 For a leading reference on the synthesis of benzocyclo-butenones, see: Alvares-Bercedo P, Flores-Gaspar A, Correa A, Martin R. J. Am. Chem. Soc. 2010; 132: 466
  • 11 For an example of this strategy in complex molecule synthesis, see: Takemura I, Imura K, Matsumoto T, Suzuki K. Org. Lett. 2004; 6: 2503
  • 12 Tripathy S, Reddy R, Durst T. Can. J. Chem. 2003; 81: 997
    • For early reports of a similar transformation, see:

    • 13a Gregoire B, Carre M.-C, Caubere P. J. Org. Chem. 1986; 51: 1419
    • 13b Carre M.-C, Gregoire B, Caubere P. J. Org. Chem. 1984; 49: 2050
    • 13c Caubere P. Acc. Chem. Res. 1974; 7: 301
  • 14 Bertolini G, Pavich G, Vergani B. J. Org. Chem. 1998; 63: 6031