Synlett 2012; 23(17): 2516-2520
DOI: 10.1055/s-0032-1317325
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Domino Carbopalladation/C–H Activation for the Synthesis of Tetrasubstituted Alkenes Bearing Five- and Seven-Membered Rings

Lutz F. Tietze*
a   Institute of Organic and Biomolecular Chemistry of the Georg-August-University Göttingen, Tammannstr. 2, 37077 Göttingen, Germany   Fax: +49(551)399476   eMail: ltietze@gwdg.de
,
Tim Hungerland
a   Institute of Organic and Biomolecular Chemistry of the Georg-August-University Göttingen, Tammannstr. 2, 37077 Göttingen, Germany   Fax: +49(551)399476   eMail: ltietze@gwdg.de
,
Christian Depken
a   Institute of Organic and Biomolecular Chemistry of the Georg-August-University Göttingen, Tammannstr. 2, 37077 Göttingen, Germany   Fax: +49(551)399476   eMail: ltietze@gwdg.de
,
Christian Maaß
b   Institute of Inorganic Chemistry of the Georg-August-University Göttingen, Tammannstr. 4, 37077 Göttingen, Germany
,
Dietmar Stalke
b   Institute of Inorganic Chemistry of the Georg-August-University Göttingen, Tammannstr. 4, 37077 Göttingen, Germany
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Publikationsverlauf

Received: 30. Juli 2012

Accepted after revision: 05. September 2012

Publikationsdatum:
28. September 2012 (online)


Abstract

A Pd-catalyzed domino carbopalladation/C–H-activation reaction of phenoxyphenyl-substituted propargylic alcohols was used for the synthesis of tetrasubstituted alkenes bearing either a dihydroindene or benzo[7]annulene motif. These compounds are of interest for the construction of molecular switches and motors.

Supporting Information

 
  • References and Notes

    • 1a Tietze LF, Ila H, Bell HP. Chem Rev. 2004; 104: 3453
    • 1b De Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions . Wiley-VCH; Weinheim: 2004
    • 1c Torborg C, Beller M. Adv. Synth. Catal. 2009; 351: 3027
    • 1d Wu X.-F, Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
    • 1e Kamba N, Iwasata T, Terao N. Chem. Soc. Rev. 2011; 40: 4937
    • 1f Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417

      For recent reviews on C–H activation, see:
    • 2a Bellina F, Rossi R. Chem. Rev. 2010; 110: 1082
    • 2b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
    • 2c Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
    • 2d Ackermann L. Chem. Rev. 2011; 111: 1315
    • 2e Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936

      For recent reviews on palladium-catalyzed domino reactions, see:
    • 3a Tietze LF. Chem. Rev. 1996; 96: 115
    • 3b Tietze LF, Brasche G, Gericke KM. Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2006
    • 3c Tietze LF, Levy L. The Mizoroki–Heck Reaction in Domino Processes . In The Mizoroki–Heck Reaction . Oestreich M. Wiley-VCH; Weinheim: 2008: 281-344
    • 3d Tietze LF, Düfert A. Pure Appl. Chem. 2010; 82: 1375
    • 3e Tietze LF, Düfert A. Domino Reactions Involving Catalytic Enantioselective Conjugate Additions. In Catalytic Asymmetric Conjugate Reactions. Cordova A. Wiley-VCH; Weinheim: 2010: 321-350
    • 3f Vlaar T, Ruijter E, Orru RV. A. Adv. Synth. Catal. 2011; 353: 809
    • 4a Saget T, Cramer N. Angew. Chem. Int. Ed. 2010; 49: 8962
    • 4b Kim B.-S, Lee S.-Y, Youn S.-W. Chem.–Asian J. 2011; 6: 1952
    • 4c Luo Y, Pan X.-L, Wu J. Org. Lett. 2011; 13: 1150
    • 4d Seashore-Ludlow B, Danielsson J, Somfai P. Adv. Synth. Catal. 2012; 354: 205
    • 4e Mahendar L, Krishna J, Reddy AG. K, Ramulu BV, Satyanarayana G. Org. Lett. 2012; 14: 628
    • 4f Lasikova A, Dohanosova J, Hlavinova L, Toffano M, Vo-Thann G, Lozisek J, Gracza T. Tetrahedron: Asymmetry 2012; 23: 818
    • 4g Giboulot S, Liron F, Prestat G, Wahl B, Sauthier M, Castanet Y, Montreux A, Poli G. Chem. Commun. 2012; 48: 5889

      For recent examples of palladium-catalyzed domino reactions including C–H activation, see:
    • 5a Tietze LF, Lotz F. Eur. J. Org. Chem. 2006; 4676
    • 5b Candito DA, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 6713
    • 5c Wang G.-W, Yuan T.-T, Li D.-D. Angew. Chem. Int. Ed. 2011; 50: 1380
    • 5d Chai DI, Thansandote P, Lautens M. Chem.–Eur. J. 2011; 17: 8175
    • 5e Lu Z, Cui Y, Jia Y. Synthesis 2011; 2595
    • 5f Liu R, Zhang J. Adv. Synth. Catal. 2011; 353: 36
    • 5g Leibeling M, Pawliczek M, Kratzert D, Stalke D, Werz DB. Org. Lett. 2012; 14: 346
    • 6a Tietze LF, Düfert A, Lotz F, Sölter L, Oum K, Lenzer T, Beck T, Herbst-Irmer R. J. Am. Chem. Soc. 2009; 131: 17879
    • 6b Tietze LF, Düfert MA, Hungerland T, Oum K, Lenzer T. Chem.–Eur. J. 2011; 17: 8452
    • 6c Tietze LF, Hungerland T, Düfert A, Objartel I, Stalke D. Chem.–Eur. J. 2012; 18: 3286
    • 7a Feringa BL, Qu D.-H. Angew. Chem. Int. Ed. 2010; 49: 1107
    • 7b Feringa BL, Browne WR. Molecular Switches 2011;
    • 7c Ruangsupapichat N, Pollard MM, Harutyunyan SR, Feringa BL. Nat. Chem. 2011; 3: 53
  • 8 For a review on C–C coupling reactions employing heterogeneous palladium catalysts, see: Yin L, Liebscher J. Chem. Rev. 2007; 107: 133

    • For recent examples about the concerted metalation–deprotonation pathway, see:
    • 9a Rousseaux S, Gorelsky SI, Chung BK. W, Fagnou K. J. Am. Chem. Soc. 2010; 132: 10692
    • 9b Lapointe D, Fagnou K. Chem. Lett. 2010; 39: 1119
    • 9c Gorelsky SI, Lapointe D, Fagnou K. J. Org. Chem. 2012; 77: 658
  • 10 CCDC-881349 (7d), CCDC-881350 (8b), and CCDC-881351 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via the internet from The Cambridge Crystallographic Data Centre (www.ccdc.cam.ac.uk/data_request/cif).
  • 11 For preparation of aldehydes 13, see: Satyanarayana G, Maier ME. Org. Lett. 2008; 10: 2361
  • 12 For preparation of enol ethers 12, see: Wünsch B. Arch. Pharm. (Weinheim, Ger.) 1990; 323: 493