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 2012; 23(19): 2735-2744
DOI: 10.1055/s-0032-1317192
DOI: 10.1055/s-0032-1317192
account
Domino Twofold Heck/6π-Electrocyclization Reactions of 1,2-Dihaloalkenes
Further Information
Publication History
Received: 13 June 2012
Accepted after revision: 15 August 2012
Publication Date:
31 October 2012 (online)
Abstract
Domino twofold Heck/6π-electrocyclization reactions of 1,2-dihaloalkenes allow for a convenient synthesis of benzene derivatives. In recent years, this strategy has been applied to various 1,2-dihalogenated carbocyclic alkenes and heterocycles, and a variety of benzo-fused ring systems have been prepared. The electrocyclization reactions proceed well for five-membered, but not for six-membered heterocycles.
1 Introduction
2 Carbocyclic Substrates
3 Heterocyclic Substrates
3.1 Thiophenes
3.2 Pyrroles
3.3 Imidazoles
3.4 Furans
3.5 Benzothiophenes
3.6 Indoles
3.7 Benzofurans
3.8 Pyridines
3.9 Pyrazines
3.10 Quinoxalines
4 Conclusions
-
References
- 1a Matsumoto S, Takahashi S, Ogura K. Heteroat. Chem. 2001; 12: 385
- 1b Lecea B, Arrieta A, Cassio FP. J. Org. Chem. 2005; 70: 1035
- 1c Vicario JL, Badia D. ChemCatChem 2010; 2: 375
- 2 For a review, see: Beaudry CM, Malerich JP, Trauner D. Chem. Rev. 2005; 105: 4757
- 3a Bishop LM, Barbarow JE, Bergman RG, Trauner D. Angew. Chem. Int. Ed. 2008; 47: 8100
- 3b Tietze LF, Beifuss U. Angew. Chem. Int. Ed. Engl. 1993; 32: 131
- 4 For a review, see: Tietze LF. Chem. Rev. 1996; 96: 115
- 5 For a review, see: de Meijere A, Zezschwitz PV, Bräse S. Acc. Chem. Res. 2005; 38: 413
- 6 Reiser O, Reichow S, de Meijere A. Angew. Chem., Int. Ed. Engl. 1987; 26: 1277
- 7 Lansky A, Reiser O, de Meijere A. Synlett 1990; 405
- 8 Voigt K, von Zezschwitz P, Rosauer K, Lansky A, Adams A, Reiser O, de Meijere A. Eur. J. Org. Chem. 1998; 1521 ; and references cited therein
- 9 Ullah I, Nawaz M, Villinger A, Langer P. Tetrahedron Lett. 2011; 52: 1888
- 10 Hussain M, Zinad DS, Salman GA, Sharif M, Villinger A, Langer P. Synlett 2010; 276
- 11 Toguem S.-MT, Hussain M, Malik I, Villinger A, Langer P. Tetrahedron Lett. 2009; 50: 4962
- 12 Billingsley K, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 3358 ; and references cited therein
- 13 Toguem S.-MT, Knepper I, Ehlers P, Dang TT, Patonay T, Langer P. Adv. Synth. Catal. 2012; 354: 1819
- 14 Toguem S.-MT, Langer P. Synlett 2011; 513
- 15 Deshpande R, Jiang L, Schmidt G, Rakovan J, Wang X, Wheeler K, Wang H. Org. Lett. 2009; 11: 4251
- 16 Toguem S.-MT, Langer P. Synlett 2010; 1779
- 17 Salman GA, Ali A, Hussain M, Khera RA, Langer P. Synthesis 2011; 2208
- 18 Hussain M, Malik I, Langer P. Synlett 2009; 2691
- 19 Kano S, Sugino E, Shibuya S, Hibino S. J. Org. Chem. 1981; 46: 3856
- 20 Pindur U, Adam R. Helv. Chim. Acta 1990; 73: 827
- 21a Hussain M, Dang TT, Langer P. Synlett 2009; 1822
- 21b Hussain M, Toguem S.-MT, Ahmad R, Tung DT, Knepper I, Villinger A, Langer P. Tetrahedron 2011; 67: 5304
- 22 Hussain M, Hung NT, Langer P. Tetrahedron Lett. 2009; 50: 3929
- 23 Ali A, Hussain M, Malik I, Fischer C, Langer P. Helv. Chim. Acta 2010; 93: 1764
- 24 Malik I, Hussain M, Ali A, Toguem S.-MT, Basha FZ, Fischer C, Langer P. Tetrahedron 2010; 66: 1637
- 25 Wang Y, Wu JI.-C, Li Q, Schleyer P.v.R. Org. Lett. 2010; 12: 4824