Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl Halides to Aryl Ketones for the Synthesis of Benzofuran Derivatives

Abstract

A nickel-catalyzed intramolecular nucleophilic addition reaction of aryl halides to aryl ketones for the formation of benzofuran derivatives has been developed. A number of substrates bearing electron-donating or electron-withdrawing groups were subjected to the standard reaction conditions, giving the corresponding products in moderate to good yields.

Key words

nickel - zinc powder - intramolecular addition - cyclization - benzofuran

Publikationsverlauf

Eingereicht: 10. November 2020

Angenommen nach Revision: 11. Dezember 2020

Artikel online veröffentlicht:
25. Januar 2021

• References

• 1a Suresh JR, Patra PK, Ila H, Junjappa H. Tetrahedron 1997; 53: 14737
• 1b Hara T, Mori K, Mizugaki T, Ebitani K, Kaneda K. Tetrahedron Lett. 2003; 44: 6207
• 1c Li J, Liu L, Ding D, Sun J, Ji Y, Dong J. Org. Lett. 2013; 15: 2884
• 2 Yasuda D, Yuasa A, Obata R, Nakajima M, Takahashi K, Ohe T, Ichimura Y, Komatsu M, Yamamoto M, Imamura R, Kojima H, Okabe T, Nagano T, Mashino T. Bioorg. Med. Chem. Lett. 2017; 27: 5006
• 3a Ha JH, Kang DW, Kim HM, Kang JM, Lee J. J. Med. Chem. 2018; 61: 396
• 3b Dai J.-R, Hallock YF, Cardellina JH, Boyd MR. J. Nat. Prod. 1998; 61: 351
• 4a Hegedu LS. Angew. Chem., Int. Ed. Engl. 1988; 27: 1113
• 4b Pindur U, Adam R. J. Heterocycl. Chem. 1988; 25: 1
• 4c Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1999; 2849
• 4d Van Order RB, Lindwa HG. Chem. Rev. 1942; 30: 69
• 4e Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000; 1045
• 4f Humphrey GR, Kuethe JT. Chem. Rev. 2006; 106: 2875
• 4g Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873
• 4h Barluenga J, Rodríguez F, Fañanás FJ. Chem. Asian J. 2009; 4: 1036
• 4i Wang ZX, Gu JZ, Jing HW, Liang YM. Synth. Commun. 2009; 39: 4079
• 4j Kraus GA, Schroeder JD. Synlett 2005; 2504
• 5a Qiao B, Zhang L, Li R. RSC Adv. 2015; 5: 93463
• 5b Elangovan S, Neumann J, Sortais J.-B, Junge K, Darcel C, Beller M. Nat. Commun. 2016; 7: 12641
• 5c Cheng XF, Peng Y, Wu J, Deng GJ. Org. Biomol. Chem. 2016; 14: 2819
• 5d Blanc A, Bénéteau V, Weibel J.-M, Pale P. Org. Biomol. Chem. 2016; 14: 9184
• 5e Jung Y, Kim I. Org. Biomol. Chem. 2016; 14: 10454
• 5f Liu GX, Lu XY. Tetrahedron 2008; 64: 7324
• 6a Metal-catalyzed cross-coupling reactions . de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004
• 6b Handbook of organopalladium chemistry for organic synthesis. Negishi E.-I. Wiley-Interscience; New York: 2002
• 7a Corriu RJ. P, Masse JP. J. J. Chem. Soc., Chem. Commun. 1972; 144a
• 7b Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
• 7c Yamamura M, Moritani I, Murahashi S.-I. J. Organomet. Chem. 1975; 91: C39
• 8a Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
• 8b Yamamoto K, Otsuka S, Nogi K, Yorimitsu H. ACS Catal. 2017; 7: 7623
• 8c Farmer JL, Pompeo M, Organ MG. Ligand Design in Metal Chemistry: Reactivity and Catalysis . Stradiotto M, Lundgren RJ. John Wiley & Sons; Chichester: 2016
• 8d King AO, Okukado N, Negishi E.-I. J. Chem. Soc., Chem. Commun. 1977; 683
• 9a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
• 9b Kotha S, Lahiri K, Kashinath D. Tetrahedron 2002; 58: 9633
• 10 Li Y, Li WD, Tian JY, Huang GZ, Lv H. Org. Lett. 2020; 22: 5353
• 11 Friedfeld MR, Shevlin M, Margulieux GW, Campeau L.-C, Chirik PJ. J. Am. Chem. Soc. 2016; 138: 3314
• 12a Majumdar KK, Cheng C.-H. Org. Lett 2000; 2: 2295
• 12b Hu JX, Wu H, Li CY, Sheng WJ, Jia YX, Gao JR. Chem. Eur. J. 2011; 17: 5234
• 12c He J.-Q, Chen C, Yu W.-B, Liu R.-R, Xu M, Li Y.-J, Gao J.-R, Jia Y.-X. Tetrahedron Lett. 2014; 55: 2805
• 12d Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
• 12e Li Z, Zhang SL, Fu Y, Guo QX, Liu L. J. Am. Chem. Soc. 2009; 131: 8815
• 12f Li Z, Liu L. Chin. J. Catal. 2015; 36: 3