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-00000084.xml
Synthesis 2013; 45(21): 2971-2976
DOI: 10.1055/s-0033-1339650
DOI: 10.1055/s-0033-1339650
paper
Ligand-Free PdCl2-Catalyzed Heck Reaction of Arylboronic Acids and Olefins under Reusable TBAB/H2O Conditions
Further Information
Publication History
Received: 10 July 2013
Accepted after revision: 31 July 2013
Publication Date:
29 August 2013 (online)

Abstract
A novel method was developed for Heck reaction of olefins and arylboronic acids using a ligand-free PdCl2 catalyst to afford the coupling products with excellent regio- and stereoselectivity. It is noteworthy that the PdCl2/CuSO4/K2CO3/TBAB/H2O system can be recovered and used for three cycles directly.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Heck RF, Nolley JP. J. Org. Chem. 1972; 37: 2320
- 1b Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
- 1c Firmansjah L, Fu GC. J. Am. Chem. Soc. 2007; 129: 11340
- 1d Min M, Kim Y, Hong S. Chem. Commun. 2013; 49: 196
- 1e Tang B, Fang X, Kuang R, Zhou X. Chin. J. Org. Chem. 2013; 33: 319
- 1f Huang Y, Song F, Wang Z, Xi P, Wu N, Wang Z, Lan J, You J. Chem. Commun. 2012; 48: 2864
- 1g Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
- 1h de Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions . Wiley-VCH; Weinheim: 2004
- 1i Beller M, Bolm C. Transition Metals for Organic Synthesis . Wiley-VCH; Weinheim: 2004
- 1j Hedrick JL, Labadie JW. Step-Growth Polymers for High-Performance Materials . American Chemical Society; Washington DC: 1996. Chap. 1, 2, and 4
- 1k Nicolaou KC, Sorensen EJ. Classics in Total Synthesis . Wiley-VCH; Weinheim: 1996. Chap. 31
- 2a Karimi B, Behzadnia H, Elhamifar D, Akhavan PF, Esfahani FK, Zamani A. Synthesis 2010; 1399
- 2b Yoo KS, Yoon CH, Jung KW. J. Am. Chem. Soc. 2006; 128: 16384
- 2c Du X, Suguro M, Hirabayashi K, Mori A. Org. Lett. 2001; 3: 3313
- 2d Cho CS, Uemura S. J. Organomet. Chem. 1994; 465: 85
- 2e Jung YC, Mishra RK, Yoon CH, Jung KW. Org. Lett. 2003; 5: 2231
- 2f Sun P, Zhu Y, Yang H, Yan H, Lu L, Zhang X, Mao J. Org. Biomol. Chem. 2012; 10: 4512
- 3a Lautens M, Roy A, Fukuoka K, Fagnou K, Martín-Matute B. J. Am. Chem. Soc. 2001; 123: 5358
- 3b Lautens M, Mancuso J, Grover H. Synthesis 2004; 2006
- 4a Zou G, Wang Z, Zhu J, Tang J. Chem. Commun. 2003; 2438
- 4b Zou G, Guo J, Wang Z, Huang W, Tang J. Dalton Trans. 2007; 3055
- 5 Amengual R, Michelet V, Genêt J.-P. Tetrahedron Lett. 2002; 43: 5905
- 6a Trivedi R, Roy S, Roy M, Sreedhar B, Kantam ML. New J. Chem. 2007; 31: 1575
- 6b Roy S, Roy M, Trivedi R. Helv. Chim. Acta 2008; 91: 1670
- 7 Gottumukkala AL, Teichert JF, Heijnen D, Eisink N, Dijk Sv, Ferrer C, Hoogenband Av.d, Minnaard AJ. J. Org. Chem. 2011; 76: 3498
- 8a Li J.-H, Tang B.-X, Tao L.-M, Xie Y.-X, Liang Y, Zhang M.-B. J. Org. Chem. 2006; 71: 7488
- 8b Tang B.-X, Wang F, Li J.-H, Xie Y.-X, Zhang M.-B. J. Org. Chem. 2007; 72: 6294