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

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.

Key words

palladium - domino reaction - C–H activation - tetra­substituted alkenes - catalysis

• 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