Synthesis of 3-Trifluoromethylbenzofurans via Palladium-Catalyzed Tandem Elimination/Annulation of β-Chloro-β-(trifluoromethyl)styrenes with 2-Halophenols

Abstract

A palladium-catalyzed tandem elimination and annulation reaction has been developed. In this way, a variety of 3-trifluoromethybenzofurans were prepared in moderate to good yields via tandem reaction of β-chloro-β-(trifluoromethyl)styrenes with 2-iodophenols and 2-bromophenols.

Key words

tandem reaction - trifluoromethyl - benzofuran - X-phos - palladium acetate - cesium carbonate

• References

• 1a Takasaki MT, Komatsu K, Tokuda H, Nishino H. Cancer Lett. 2000; 158: 53
• 1b Carter GA, Chamberlain K, Wain RL. Ann. Appl. Biol. 1978; 88: 57
• 1c Cho JY, Kim AR, Yoo ES, Baik KU, Park MH. A. J. Pharm. Pharmacol. 1999; 51: 1267
• 2a Ward RS. Nat. Prod. Rep. 1990; 7: 349
• 2b Ward RS. Nat. Prod. Rep. 1993; 10: 183
• 2c Muhammad I, Li X.-C, Jacob MR, Tekwani BL, Dunbar DC, Ferreira D. J. Nat. Prod. 2003; 66: 804
• 2d Navarro E, Alonso SJ, Trujillo J, Jorge E, Perez C. J. Nat. Prod. 2001; 64: 134
• 2e Zacchino S, Rodriguez G, Pezzenati G, Orellana G, Enriz R, Gonzalez SM. J. Nat. Prod. 1997; 60: 659
• 2f Banskota A, Tezuka Y, Midorikawa K, Matsushige K, Kadota S. J. Nat. Prod. 2000; 63: 1277
• 3a Liang Y, Tang S, Zhang X.-D, Mao L.-Q, Xie Y.-X, Li J.-H. Org. Lett. 2006; 8: 3017
• 3b Chen C, Dormer PG. J. Org. Chem. 2005; 70: 6964
• 3c Okitsu T, Nakazawa D, Taniguchi R, Wada A. Org. Lett. 2008; 10: 4967
• 3d Sakai N, Uchida N, Konakahara T. Tetrahedron Lett. 2008; 49: 3437
• 3e De Luca L, Giacomelli G, Nieddu G. J. Org. Chem. 2007; 72: 3955
• 3f Nakamura I, Mizushima Y, Yamamoto Y. J. Am. Chem. Soc. 2005; 127: 15022
• 3g Fürstner A, Davies PW. J. Am. Chem. Soc. 2005; 127: 15024
• 3h Huang XC, Liu YL, Liang Y, Pi SF, Wang F, Li JH. Org. Lett. 2008; 10: 1525
• 3i Bates CG, Saejueng P, Murphy JM, Venkataraman D. Org. Lett. 2002; 4: 4727
• 4a Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
• 4b Hagmann WK. J. Med. Chem. 2008; 51: 4359
• 4c Muller K, Faeh C, Diederich F. Science 2007; 317: 1881
• 4d Schlosser M. Angew. Chem. Int. Ed. 2005; 44: 214
• 5 Mejía E, Togni A. ACS Catal. 2012; 2: 521
• 6 Jiang Z.-X, Qing F.-L. J. Fluorine Chem. 2003; 123: 57
• 7a Kobatake T, Fujino D, Yoshida S, Yorimitsu H, Oshima K. J. Am. Chem. Soc. 2010; 132: 11840
• 7b Ookubo Y, Wakamiya A, Yorimitsu H, Osuka A. Chem. Eur. J. 2012; 18: 12690
• 8 Konno T, Chae J, Ishihara T, Yamanaka H. Tetrahedron 2004; 60: 11695
• 9a Dong S.-X, Zhang X.-G, Liu Q, Tang R.-Y, Zhong P, Li J.-H. Synthesis 2010; 1521
• 9b Li C.-L, Zhang X.-G, Tang R.-Y, Zhong P, Li J.-H. J. Org. Chem. 2010; 75: 7037
• 9c Sun L.-L, Liao Z.-Y, Tang R.-Y, Deng C.-L, Zhang X.-G. J. Org. Chem. 2012; 77: 2850
• 9d Wang W.-Y, Sun L.-L, Deng C.-L, Tang R.-Y, Zhang X.-G. Synthesis 2013; 45: 118
• 9e Sun L.-L, Hu BL, Tang R.-Y, Deng C.-L, Zhang X.-G. Adv. Synth. Catal. 2013; 355: 377
• 10 Meazza G, Capuzzi L, Piccardi P. Synthesis 1989; 331
• 11 Konno T, Chae J, Kanda M, Nagai G, Tamura K, Ishihara T, Yamanaka H. Tetrahedron 2003; 59: 7571