Furans to Benzofurans: Intramolecular Cross-Benzoin Reactions Catalysed by N-Heterocyclic Carbenes

Abstract

The first synthesis of dihydrobenzofuranones and benzofurans based on an intramolecular cross-benzoin reaction has been reported. Commercially available 3-furan carboxaldehydes are readily α-alkylated to furnish 3-formyl-2-furylcarbinols, which are further elaborated to the synthesis of benzofurans in good yields through sequential bismuth(III) chloride catalysed furfurylation and a novel NHC-promoted intramolecular cross-benzoin condensation reaction.

Key words

furans - N-heterocyclic carbenes - annulation - benzoin condensation - organocatalysis

• References

• 1 These authors contributed equally to this article.
• 2a Menon RS, Biju AT, Nair V. Chem. Soc. Rev. 2015; 44: 5040
• 2b Mahatthananchai J, Bode JW. Acc. Chem. Res. 2014; 47: 696
• 2c Loh CC. J, Enders D. Chem. Eur. J. 2012; 18: 10212
• 2d Ryan SJ, Candish L, Lupton DW. Chem. Soc. Rev. 2013; 42: 4906
• 2e Cohen DT, Scheidt KA. Chem. Sci. 2012; 3: 53
• 2f Vora HU, Rovis T. Aldrichimica Acta 2011; 44: 3
• 2g Marion N, Diez-Gonzalez S, Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2988
• 2h Sarkar SD, Studer A. Angew. Chem. Int. Ed. 2010; 49: 9266
• 2i Enders D, Niemeier O, Hanseler A. Chem. Rev. 2007; 107: 5606
• 2j Phillips EM, Chan A, Scheidt KA. Aldrichimica Acta 2009; 42: 55
• 2k Moore JL, Rovis T. Top. Curr. Chem. 2010; 291: 77
• 2l Nair V, Menon RS, Biju AT, Sinu CR, Paul RR, Jose A, Sreekumar V. Chem. Soc. Rev. 2011; 40: 5336
• 2m Vora HU, Wheeler P, Rovis T. Adv. Synth. Catal. 2012; 354: 1617
• 2n Bugaut X, Glorius F. Chem. Soc. Rev. 2012; 41: 3511
• 2o Izquierdo J, Hutson GE, Cohen DT, Scheidt KA. Angew. Chem. Int. Ed. 2012; 51: 11686
• 2p Ramanjaneyulu BT, Reddy V, Arde P, Mahesh S, Anand RV. Chem. Asian J. 2013; 8: 1489
• 2q Ramanjaneyulu BT, Reddy V, Saxena A, Anand RV. Org. Biomol. Chem. 2012; 10: 848
• 3 Ukai T, Tanaka S, Dokawa S. J. Pharm. Soc. Jpn. 1943; 63: 269
• 4a Collett CJ, Massey RS, Taylor JE, Maguire OR, O’Donoghue AC, Smith AD. Angew. Chem. Int. Ed. 2015; 54: 6887
• 4b Liu T, Han S.-M, Han L.-L, Wang L, Cui X.-Y, Du C.-Y, Bi S. Org. Biomol. Chem. 2015; 13: 3654
• 4c Flanigan DM, Romanov-Michailidis F, White NA, Rovis T. Chem. Rev. 2015; 115: 9307
• 4d Goodman CG, Johnson JS. J. Am. Chem. Soc. 2014; 136: 14698
• 4e Thai K, Langdon SM, Bilodeau F, Gravel M. Org. Lett. 2013; 15: 2214
• 4f Piel I, Pawelczyk MD, Hirano K, Froehlich R, Glorius F. Eur. J. Org. Chem. 2011; 5475
• 4g Biju AT, Kuhl N, Glorius F. Acc. Chem. Res. 2011; 44: 1182
• 4h Enders D, Grossmann A, Huang H, Raabe G. Eur. J. Org. Chem. 2011; 4298
• 4i Sanchez-Diez E, Fernandez M, Uria U, Reyes E, Carrillo L, Vicario JL. Chem. Eur. J. 2015; 21: 8384
• 4j Xu J, Mou C, Zhu T, Song B.-A, Chi YR. Org. Lett. 2014; 16: 3272
• 4k Langdon SM, Wilde MM. D, Thai K, Gravel M. J. Am. Chem. Soc. 2014; 136: 7539
• 4l Padmanaban M, Biju AT, Glorius F. Org. Lett. 2011; 13: 98
• 4m Enders D, Grossmann A, Fronert J, Raabe G. Chem. Commun. 2010; 6282
• 4n Enders D, Henseler A. Adv. Synth. Catal. 2009; 351: 1749
• 4o Li G.-Q, Dai L.-X, You S.-L. Chem. Commun. 2007; 852
• 4p Mennen SM, Miller SJ. J. Org. Chem. 2007; 72: 5260
• 4q Rose CA, Gundala S, Connon SJ, Zeitler K. Synthesis 2011; 190
• 4r Bortolini O, Fantin G, Fogagnolo M, Giovannini PP, Venturi V, Pacifico S, Massi A. Tetrahedron 2011; 67: 8110
• 4s Ramanjaneyulu BT, Mahesh S, Anand RV. Org. Lett. 2015; 17: 6

For examples on the intramolecular cross-benzoin reaction between aldehydes and ketones, see:
• 5a Hachisu Y, Bode JW, Suzuki K. J. Am. Chem. Soc. 2003; 125: 8432
• 5b Enders D, Niemeier O. Synlett 2004; 2111
• 5c Enders D, Niemeier O, Raabe G. Synlett 2006; 2431
• 5d Enders D, Niemeier O, Balensiefer T. Angew. Chem. Int. Ed. 2006; 45: 1463
• 5e Takikawa H, Hachisu Y, Bode JW, Suzuki K. Angew. Chem. Int. Ed. 2006; 45: 3492
• 5f Takikawa H, Suzuki K. Org. Lett. 2007; 9: 2713
• 5g Li Y, Feng Z, You S.-L. Chem. Commun. 2008; 2263
• 5h Ema T, Oue Y, Akihara K, Miyazaki Y, Sakai T. Org. Lett. 2009; 11: 4866
• 5i Takada A, Hashimoto Y, Takikawa H, Hikita K, Suzuki K. Angew. Chem. Int. Ed. 2011; 50: 2297
• 6a Lipshutz BH. Chem. Rev. 1986; 86: 795
• 6b Nagahara T, Yokoyama Y, Inamura K, Katakura S, Komoriya S, Yamaguchi H, Hara T, Iwamoto M. J. Med. Chem. 1994; 37: 1200
• 6c Hanson JR. Nat. Prod. Rep. 1995; 12: 381
• 6d Hou XL, Cheung HY, Hon TY, Kwan PL, Lo TH, Tong SY, Wong HN. C. Tetrahedron 1998; 54: 1955
• 6e Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 2001; 2491
• 6f Watanabe M, Su WT, Chang YJ, Chao TH, Wen YS, Chow TJ. Chem. Asian J. 2013; 8: 60
• 6g Simonetti SO, Larghi EL, Bracca AB. J, Kaufman TS. Nat. Prod. Rep. 2013; 30: 941
• 6h Han P, Gong X, Lin B, Jia Z, Ye S, Sun Y, Yanga H. RSC Adv. 2015; 5: 50098
• 6i Radadiya A, Shah A. Eur. J. Med. Chem. 2015; 97: 356
• 6j Khanam H Shamsuzzaman Eur. J. Med. Chem. 2015; 97: 483
• 6k Nevagi RJ, Dighe SN, Dighe SN. Eur. J. Med. Chem. 2015; 97: 561
• 6l Hiremathad A, Patil MR, Chethana KR, Chand K, Santos MA, Keri RS. RSC Adv. 2015; 5: 96809
• 7a Sakamoto T, Kondo Y, Yamanaka H. Heterocycles 1988; 27: 2225
• 7b Nematollahi D, Habibi D, Rahmati M, Rafiee M. J. Org. Chem. 2004; 69: 2637
• 7c Cacchi S, Fabrizi G, Goggiamani A. Curr. Org. Chem. 2006; 10: 1423
• 7d Nagamochi M, Fang YQ, Lautens M. Org. Lett. 2007; 9: 2955
• 7e Liu Y, Wang M, Yuan H, Liu Q. Adv. Synth. Catal. 2010; 352: 884
• 7f Cacchi S, Fabrizi G, Goggiamani A. Org. Biomol. Chem. 2011; 9: 641
• 7g Kuram MR, Bhanuchandra M, Sahoo AK. Angew. Chem. Int. Ed. 2013; 52: 4607
• 7h Sharma U, Naveen T, Maji A, Manna S, Maiti D. Angew. Chem. Int. Ed. 2013; 52: 12669
• 7i Gao Y, Xiong W, Chen H, Wu W, Peng J, Gao Y, Jiang H. J. Org. Chem. 2015; 80: 7456
• 8a Dhiman S, Ramasastry SS. V. Indian J. Chem., Sect. A 2013; 52: 1103
• 8b Shirke RP, Ramasastry SS. V. J. Org. Chem. 2015; 80: 4893
• 9a Hashmi AS. K, Enns E, Frost TM, Schäfer S, Frey W, Rominger F. Synthesis 2008; 2707
• 9b Shaik FH, Kar GK. Beilstein J. Org. Chem. 2009; 5: 47
• 9c Guzmán JA, Taylor JE, Tillman JE, France S. Org. Lett. 2014; 16: 3788
• 9d Sen S, Vorogushin A, Swanson E, Pulley SR. Org. Lett. 1999; 1: 1721
• 9e Grenzer EM, Gantzel PK, Harvey DF. J. Am. Chem. Soc. 1994; 116: 6719
• 9f Brisbois RG, Kowalczyk JJ, Miller RF, Danheiser RL. J. Am. Chem. Soc. 1990; 112: 3094
• 9g Benitez A, Herrera FR, Romero M, Talamas FX. J. Org. Chem. 1996; 61: 1487
• 9h For an interesting transformation of benzofurans into furans, see: Dhiman S, Ramasastry SS. V. J. Org. Chem. 2013; 78: 10427
• 10 Dhiman S, Ramasastry SS. V. Org. Biomol. Chem. 2013; 11: 4299
• 11 For a recent review, see: Büschleb M, Dorich S, Hanessian S, Tao D, Schenthal KB, Overman LE. Angew. Chem. Int. Ed. 2016; 55: 4156
• 12 CCDC 1454583 (for 2e) contains the supplementary crystallographic data. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
• 13 Shing TK. M, Cheng HM, Wong WF, Kwong CS. K, Li J, Lau CB. S, Leung PS, Cheng CH. K. Org. Lett. 2008; 10: 3145

For dasycarpuside A, see:
• 14a Chang J, Xuan LJ, Xu YM, Zhang JS. Planta Med. 2002; 68: 425
• 14b For the hepatic agent, see: Iwasaki T, Sugiura M, Matsuoka Y, Matsumoto M, Kitamura K. Eur. Pat. Appl EP386778, 1990
• 14c For angelicins, see: Guiotto A, Rodighiero P, Manzini P, Pastohi G, Bordin F, Baccichetti F, Carlassare F, Vedaldi D, Dall’Acqua F, Tamaro M, Recchia G, Cristofolini M. J. Med. Chem. 1984; 27: 959