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 2012; 44(17): 2707-2712
DOI: 10.1055/s-0032-1316753
DOI: 10.1055/s-0032-1316753
paper
Benzyl-Type Cation Initiated Nucleophilic Substitution on Furan and Thiophene by Using α-EWG Ketene S,S-Acetals as Nucleophiles
Further Information
Publication History
Received: 27 April 2012
Accepted after revision: 26 June 2012
Publication Date:
03 August 2012 (online)
Abstract
An efficient method for introducing nucleophiles on furan and thiophene has been established via the in situ formation of benzyl-type carbocation, delocalization of the carbocation on heterocyclic ring, and nucleophilic trap of α-EWG ketene S,S-acetal sequence at the 5-position.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Dean FM. Naturally Occurring Oxygen Ring Compounds . Butterworths; London: 1963: 1-28
- 1b Meegan MJ, Donnelly DM. X In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Rees CW. Pergamon Press; New York: 1984: 657-712
- 1c Reid ST In Comprehensive Heterocyclic Chemistry . Vol. 3. Katritzky AR, Rees CW. Academic Press; New York: 1983: 1-95
- 2a Lipshutz BH. Chem. Rev. 1986; 86: 795
- 2b Rassu G, Zanardi F, Battistini L, Casiraghi G. Chem. Soc. Rev. 2000; 29: 109
- 3a Rodríguez AR, Spur BW. Tetrahedron Lett. 2003; 44: 7411
- 3b Roberts-Bleming SJ, Davies GL, Kalaji M, Murphy PJ, Celli AM, Donati D, Ponticelli F. J. Org. Chem. 2003; 68: 7115
- 3c Moeller KD, Mihelcic J. J. Am. Chem. Soc. 2003; 125: 37
- 4a Apsel B, Bender JA, Escobar M, Kaelin DE. Jr, Lopez OD, Martin SF. Tetrahedron Lett. 2003; 44: 1075
- 4b Krishna UM, Srikanth GS. C, Trivedi GK, Deodhar KD. Synlett 2003; 2383
- 4c Ponomarenko S, Kirchmeyer S. J. Mater. Chem. 2003; 13: 197
- 5a Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
- 5b Jørgensen M, Lee S, Liu X, Wolkowski JP, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 12557
- 5c Glover B, Harvey KA, Liu B, Sharp MJ, Tymoschenko MF. Org. Lett. 2003; 5: 301
- 6a Makosza M, Staliński K. Synthesis 1998; 1631
- 6b Lawrence NJ, Lamarche O, Thurrab N. Chem. Commun. 1999; 689
- 6c Migaud ME, Wilmouth RC, Mills GI, Wayne GJ, Risley C, Chambers C, Macdonald SJ. F, Schofield CJ. Chem. Commun. 2002; 1274
- 6d Moosa BA, Abu Safieh KA, El-Abadelah MM. Heterocycles 2002; 57: 1831
- 7 Akai S, Kawashita N, Satoh H, Wada Y, Kakiguchi K, Kuriwaki I, Kita Y. Org. Lett. 2004; 6: 3793
- 8 Divald S, Chun MC, Joullié MM. J. Org. Chem. 1976; 41: 2835
- 9a Palmer LI, Read de Alaniz J. Angew. Chem. Int. Ed. 2011; 50: 7167
- 9b Yin BL, Lai JQ, Zhang ZR, Jiang HF. Adv. Synth. Catal. 2011; 353: 1961
- 10a Pan L, Liu Q. Synlett 2011; 1073
- 10b Dieter RK. Tetrahedron 1986; 42: 3029
-
10c Junjappa H, Ila H, Asokan CV. Tetrahedron 1990; 46: 5423
- 10d Kolb M. Synthesis 1990; 171
- 11a Fu Z, Wang M, Ma Y, Liu Q, Liu J. J. Org. Chem. 2008; 73, 7625
-
11b Ma Y, Wang M, Li D, Bekturhun B, Liu J, Liu Q. J. Org. Chem. 2009; 74: 3116
- 11c Yuan H.-J, Wang M, Liu Y.-J, Liu Q. Adv. Synth. Catal. 2009; 351: 112
- 11d Liu Y, Wang M, Yuan H, Liu Q. Adv. Synth. Catal. 2010; 352: 884
- 11e Liang D, Wang M, Bekturhun B, Xiong B, Liu Q. Adv. Synth. Catal. 2010; 352: 1593
- 11f Yuan H, Wang M, Liu Y, Wang L, Liu J, Liu Q. Chem.–Eur. J. 2010; 16: 13450
- 11g Wang M, Sun S, Liang D, Liu B, Dong Y, Liu Q. Eur. J. Org. Chem. 2011; 2466
- 12a Yin Y, Wang M, Liu Q, Hu J, Sun S, Kang J. Tetrahedron Lett. 2005; 46: 4399
- 12b Sun S, Zhang Q, Liu Q, Kang J, Yin Y, Li D, Dong D. Tetrahedron Lett. 2005; 46: 6271
- 12c Yin Y, Zhang Q, Li J, Sun S, Liu Q. Tetrahedron Lett. 2006; 47: 6071
- 12d Zhang Q, Liu Y, Wang M, Liu Q, Hu J, Yin Y. Synthesis 2006; 1090
- 12e Zhang Q, Sun S, Hu J, Liu Q, Tan J. J. Org. Chem. 2007; 72: 139
- 13 Sun S, Wang M, Deng H, Liu Q. Synthesis 2008; 573
- 14a Basavaiah D, Rao PD, Hyma RS. Tetrahedron 1996; 52: 8001
- 14b Langer P. Angew. Chem. Int. Ed. 2000; 39: 3049
- 14c Basavaiah D, Rao AJ, Satyanarayana T. Chem. Rev. 2003; 103: 811
-
14d Basavaiah D, Reddy BS, Badsara SS. Chem. Rev. 2010; 110: 5447
- 15 X-ray diffraction data for 3a have been deposited at the Cambridge Crystallographic Data Centre with supplementary publication number of CCDC 860063. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (internat.) +44(1223)336 033; E-mail: deposit@ccdc.cam.ac.uk]. The CIF files are also available in the Supporting Information.
- 16 Aggarwal V, Mereu A. Chem. Commun. 1999; 2311
For reviews, see:
For reviews, see:
For reviews on the Baylis–Hillman reactions, see: