Synthesis of Substituted Indenes and cis-Stilbenoid Hydrocarbons via Palladium-Catalyzed Domino Reactions of Hindered Grignard Reagents with (E)-1,2-Dibromoethenes

Abstract

Palladium-catalyzed domino reactions of (E)-1,2-dibromoethenes with hindered Grignard reagents based on carbopalladation, palladium-catalyzed cross-coupling, and C-H activation are described. These domino reactions could be influenced by the ligand, reaction temperature, nucleophilicity of Grignard reagents, and steric hindrance of the substrates. Our study provides an efficient access to some useful polysubstituted indenes and cis-substituted stilbenes, and may be useful for the development of other cross-coupling and C-H activation-based tandem/domino reactions.

Key words

palladium - Grignard reactions - domino reactions - cyclization­ - cross-coupling

References

• 1a Transition Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; New York: 1998. 
• 1b Beller M. Bolm C. Transition Metals for Organic Synthesis   Wiley-VCH; Weinheim: 1998. 
• 1c Collman JP. Hegedus LS. Norton JR. Finke RG. Principles and Applications of Organotransition Metal Chemistry   University Science Books; Mill Valley CA: 1987. 
• 2a Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4442 
• 2b Hu Q.-S. In Synthetic Methods for Step-Growth Polymers   Rogers M. Long T. Wiley; New York: 2003.  p.467-526  
• 3 Dong C.-G. Hu Q.-S. J. Am. Chem. Soc.  2005,  127:  10006 
• 4a Dong C.-G. Hu Q.-S. Tetrahedron  2008,  64:  2537 
• 4b Hu Q.-S. Synlett  2007,  1131 
• 4c Dong C.-G. Hu Q.-S. Angew. Chem. Int. Ed.  2006,  45:  2289 
• 4d Dong C.-G. Hu Q.-S. Org. Lett.  2006,  8:  5057 
• 5a He P. Lu Y. Dong C.-G. Hu Q.-S. Org. Lett.  2007,  9:  343 
• 5b He P. Lu Y. Hu Q.-S. Tetrahedron Lett.  2007,  48:  5283 
• 6 Dong CG. Yeung P. Hu Q.-S. Org. Lett.  2007,  9:  363 
• 7a Wasilke J.-C. Obrey SJ. Baker RT. Bazan GC. Chem. Rev.  2005,  105:  1001 
• 7b Tietze LF. Rackelmann N. Pure Appl. Chem.  2004,  76:  1967 
• 7c Nicolaou KC. Montagnon T. Snyder SA. Chem. Commun.  2003,  551 
• 7d Parsons PJ. Penkett CS. Shell AJ. Chem. Rev.  1996,  96:  195 
• 7e Tietze LF. Chem. Rev.  1996,  96:  115 ; and references cited therein
• 8a de Meijere A. von Zezschwitz P. Bräse S. Acc. Chem. Res.  2005,  38:  413 
• 8b Ritleng V. Sirlin C. Pfeffer M. Chem. Rev.  2002,  102:  1731 
• 8c Ikeda S.-i. Acc. Chem. Res.  2000,  33:  511 
• 8d Montgomery J. Acc. Chem. Res.  2000,  33:  467 
• 8e Heumann A. Reglier M. Tetrahedron  1996,  52:  9289 
• 8f Malacria M. Chem. Rev.  1996,  96:  289 ; and references cited therein
• Selected recent examples of palladium-catalyzed tandem/domino reactions:
• 9a Mariampillai B. Alberico D. Bidau V. Lautens M. J. Am. Chem. Soc.  2006,  128:  14436 
• 9b Bertrand MB. Wolfe JP. Org. Lett.  2006,  8:  2353 
• 9c Leclerc J.-P. Andre M. Fagnou K. J. Org. Chem.  2006,  71:  1711 
• 9d Henderson JL. Edwards AS. Greaney MF. J. Am. Chem. Soc.  2006,  128:  7426 
• 9e Pinto A. Neuville L. Retailleau P. Zhu J. Org. Lett.  2006,  8:  4927 
• 9f Martins A. Marquardt U. Kasravi N. Alberico D. Lautens M. J. Org. Chem.  2006,  71:  4937 
• 9g Hay MB. Wolfe JP. J. Am. Chem. Soc.  2005,  127:  16468 
• 9h Tsang WCP. Zheng N. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  14560 
• 9i Bressy C. Alberico D. Lautens M. J. Am. Chem. Soc.  2005,  127:  13148 
• 9j Zhao J. Larock RC. Org. Lett.  2005,  7:  701 
• 9k Ohno H. Yamamoto M. Iuchi M. Tanaka T. Angew. Chem. Int. Ed.  2005,  44:  5103 
• 9l Yang Q. Ney JE. Wolfe JP. Org. Lett.  2005,  7:  2575 
• 9m Cheung WS. Patch RJ. Player MR. J. Org. Chem.  2005,  70:  3741 
• 9n Ganton MD. Kerr MA. Org. Lett.  2005,  7:  4777 
• 9o Abbiati G. Arcadi A. Canevari V. Capezzuto L. Rossi E. J. Org. Chem.  2005,  70:  6454 
• 9p Huang Q. Fazio A. Dai G. Campo MA. Larock RC. J. Am. Chem. Soc.  2004,  126:  7460 
• 9q Wolfe JP. Rossi MA. J. Am. Chem. Soc.  2004,  126:  1620 
• 9r Ney JE. Wolfe JP. Angew. Chem. Int. Ed.  2004,  43:  3605 
• 10 For recent reviews for carbopalladation of alkynes see ref 8a and: Zeni G. Larock RC. Chem. Rev.  2004,  104:  2285 
• Recent reviews for C-H activation see ref 8b and:
• 11a Handbook of C-H Transformations: Application in Organic Synthesis   Vol. 2:  Dyker G. Wiley-VCH; Weinheim: 2005. 
• 11b Kakiuchi F. Chatani N. Adv. Synth. Catal.  2003,  345:  1077 
• 11c Jia C. Kitamura T. Fujiwara Y. Acc. Chem. Res.  2001,  34:  633 
• 12a Alt HG. Köppl A. Chem. Rev.  2000,  100:  1205 
• 12b Korte A. Legros J. Bolm C. Synlett  2004,  2397 ; and references therein
• 12c Barbera J. Rakitin OA. Ros MB. Torroba T. Angew. Chem. Int. Ed.  1998,  37:  296 
• Substituted indenes were typically prepared in more than one step. For recent examples of one-pot access to substituted indenes with different substitution patterns: From 2-(2-(1-alkynyl)phenyl)malonates or 2-(2-halo­-phenyl)malonate:
• 13a Guo L.-N. Duan X.-H. Bi H.-P. Liu X.-Y. Liang Y.-M. J. Org. Chem.  2006,  71:  3325 
• 13b Zhang D. Yum EK. Liu Z. Larock RC. Org. Lett.  2005,  7:  4963 
• Also see:
• 13c Kuninobu Y. Nishina Y. Takai K. Org. Lett.  2006,  8:  2891 
• 13d Nakamura I. Bajracharya GB. Wu H. Oishi K. Mizushima Y. Gridnev ID. Yamamoto Y. J. Am. Chem. Soc.  2004,  126:  15423 
• 14a Rathore R. Lindeman SV. Kochi JK. Angew. Chem. Int. Ed.  1998,  37:  1585 ; Angew. Chem. 1998, 110, 1665
• 14b Irie M. Chem. Rev.  2000,  100:  1685 
• The most efficient preparation methods reported so far involve the use of 1,2-dibromoalkenes with hindered Grignard reagents:
• 15a Rathore R. Deselnicu MI. Burns CL. J. Am. Chem. Soc.  2002,  124:  14832 
• For other methods:
• 15b Maeda K. Okamoto Y. Morlender N. Haddad N. Eventova I. Biali SE. Rappoport Z. J. Am. Chem. Soc.  1995,  117:  9686 
• 15c Bottino FA. Finocchiaro P. Libertini E. Reale A. Recca A. J. Chem. Soc., Perkin Trans. 2  1982,  77 
• 16a Organ MG. Ghasemi H. Valente C. Tetrahedron  2004,  60:  9453 
• 16b Andreini BP. Benetti M. Carpita A. Rossi R. Gazz. Chim. Ital.  1988,  118:  469 
• 17 A similar regioselectivity trend was observed in palladium-catalyzed domino reaction of internal alkynes and aryl­-boronic acids: Zhou C. Larock RC. J. Org. Chem.  2005,  70:  3765 ; also see ref 6
• Three-membered aryne-Pd(0) complexes have been previously proposed as intermediates. For examples:
• 18a Liu Z. Larock RC. J. Org. Chem.  2007,  72:  223 
• 18b Liu Z. Zhang X. Larock RC. J. Am. Chem. Soc.  2005,  127:  15716 
• 18c Zhang X. Larock RC. Org. Lett.  2005,  7:  3973