Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2014; 25(07): 1009-1013
DOI: 10.1055/s-0033-1340830
DOI: 10.1055/s-0033-1340830
letter
Palladium-Catalyzed Synthesis of Indene Derivatives via Intramolecular Allylic Arylation of Baylis–Hillman Acetates
Further Information
Publication History
Received: 08 December 2013
Accepted after revision: 23 January 2014
Publication Date:
13 February 2014 (online)
Abstract
An intramolecular allylic arylation protocol for the synthesis of indene derivatives from readily available Baylis–Hillman acetates via palladium-catalyzed C–H bond activation has been developed.
Key words
palladium - C–H bond activation - indene derivatives - Baylis–Hillman acetates - intramolecular allylic arylationSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Barberá J, Rakitin OA, Ros MB, Ros NB, Torroba T. Angew. Chem. Int. Ed. 1998; 37: 296
- 2a Harrowven DC, Newman NA, Knight CA. Tetrahedron Lett. 1998; 39: 6757
- 2b Karaguni IM, Glusenkamp KH, Langerak A, Geisen C, Ullrich V, Winde G, Moroy T, Muller O. Bioorg. Med. Chem. Lett. 2002; 12: 709
- 2c Kolanos R, Siripurapu U, Pullagurla M, Riaz M, Setola V, Roth BL, Dukat M, Glennon RA. Bioorg. Med. Chem. Lett. 2005; 15: 1987
- 2d Wang Y, Mo S, Wang YS, Li JS, Yang YC, Shi JG. Org. Lett. 2005; 7: 1675
- 3a Zargarian D. Coord. Chem. Rev. 2002; 157: 233
- 3b Alt HG, Köppl A. Chem. Rev. 2000; 100: 1205
- 3c Wang BQ. Coord. Chem. Rev. 2006; 250: 242
- 4a Skattebøl L, Boulette B. J. Org. Chem. 1966; 31: 81
- 4b Padwa A, Blacklock TJ, Loza R. J. Org. Chem. 1982; 47: 3712
- 4c Lu JM, Shi M. Org. Lett. 2006; 8: 5317
- 4d Yadav VK, Kumar NV, Parvez M. Chem. Commun. 2007; 22: 2281
- 4e Zhu ZB, Shi M. Chem. Eur. J. 2008; 14: 10219
- 4f Hu B, Xing SY, Wang ZW. Org. Lett. 2008; 10: 5481
- 4g Wang J, Zhang L, Jing Y, Huang W, Zhou X. Tetrahedron Lett. 2009; 50: 4978
- 5a Seomoon D, Lee K, Kim H, Lee PH. Chem. Eur. J. 2007; 13: 5197
- 5b Kuninobu Y, Nishina Y, Shouho M, Takai K. Angew. Chem. Int. Ed. 2006; 45: 2766
- 5c Kuninobu Y, Kawata A, Takai K. J. Am. Chem. Soc. 2005; 127: 13498
- 5d Kuninobu Y, Tokunaga Y, Kawata A, Takai K. J. Am. Chem. Soc. 2006; 128: 202
- 5e Duan XH, Guo LN, Bi HP, Liu XY, Liang YM. Org. Lett. 2006; 8: 3053
- 5f Guo LN, Duan XH, Bi HP, Liu XY, Liang YM. J. Org. Chem. 2006; 71: 3325
- 5g Zhang DH, Liu ZJ, Yum EK, Larock RC. J. Org. Chem. 2007; 72: 251
- 5h Guan ZH, Ren ZH, Zhao LB, Liang YM. Org. Biomol. Chem. 2008; 6: 1040
- 5i Rayabarapu DK, Cheng CH. Chem. Commun. 2002; 9: 942
- 5j Chang KJ, Rayabarapu DK, Cheng CH. J. Org. Chem. 2004; 69: 4781
- 5k Dubé P, Toste FD. J. Am. Chem. Soc. 2006; 128: 12062
- 6 Dethe DH, Murhade G. Org. Lett. 2013; 15: 429
- 7 Zhao J, Clark DA. Org. Lett. 2012; 14: 1668
- 8 Eom D, Park S, Park Y, Ryu T, Lee PH. Org. Lett. 2012; 14: 5392
- 9 Magar KB. S, Lee YR. Org. Lett. 2013; 15: 4288
- 10a Liu C.-R, Yang F.-L, Jin Y.-Z, Ma X.-T, Cheng D.-J, Li N, Tian S.-K. Org. Lett. 2010; 12: 3832
- 10b Sun Z.-M, Chen S.-P, Zhao P. Chem. Eur. J. 2010; 16: 2619
- 10c Muralirajan K, Parthasarathy K, Cheng C.-H. Angew. Chem. Int. Ed. 2011; 50: 4169
- 10d Patureau FW, Besset T, Kuhl N, Glorius F. J. Am. Chem. Soc. 2011; 133: 2154
- 10e Tran DN, Cramer N. Angew. Chem. Int. Ed. 2011; 50: 11098
- 10f Zhao P, Wang F, Han K, Li X. Org. Lett. 2012; 14: 5506
- 11a Li XQ, Xu XS, Zhou C. Chem. Commun. 2012; 48: 12240
- 11b Xu XS, Li XQ, Yan XH, Wang HS, Deng Y, Shao JB. Synlett 2011; 3026
- 12 Smith CD, Rosocha G, Mui L, Batey RA. J. Org. Chem. 2010; 75: 4716 ; and references cited therein
- 13 General Procedure for the Intramolecular Allylic Alkylation of Baylis–Hillman Acetates Baylis–Hillman acetate (0.5 mmol), Pd(OAc)2 (5.6 mg, 0.025 mmol), K2CO3 (69 mg, 0.5 mmol), and Ph3P (26.2 mg, 0.1 mmol) were placed in a Schlenk tube. The reaction vessel was purged with argon, and dioxane (2.0 mL) was added. After the reaction mixture was stirred at 110 °C for 10 h, the solvent was removed under reduced pressure, and the residual was purified by silica gel chromatography (EtOAc–PE = 1:20) to give indenes 2.
- 14 Suzuki Y, Nemoto TK, Kakugawa A, Hamajima J, Hamada Y. Org. Lett. 2012; 14: 2350
- 15 Akermark B, Hansson S, Vitagliano A. J. Am. Chem. Soc. 1990; 112: 4587