Recyclable Palladium-Catalyzed Carbonylative Cyclization of Aryl Iodides and 2-Hydroxyacetophenones towards Flavones

Abstract

A highly efficient heterogeneous palladium-catalyzed carbonylative cyclization of aryl iodides and 2-hydroxyacetophenones is developed. The reaction proceeds efficiently in DMSO at 120 °C under 3 bar of carbon monoxide by using 2 mol% of an MCM-41-immobilized bidentate phosphine palladium complex [MCM-41-2P-Pd(OAc)₂] as the catalyst and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base, providing a general, efficient and practical approach for the assembly of a wide variety of flavones in mostly good to high yields from readily available starting materials. This supported palladium catalyst can be easily recovered via centrifugation of the reaction mixture and recycled more than nine times without any significant loss of its catalytic efficiency.

Key words

palladium - carbonylative cyclization - flavones - aryl iodide - heterogeneous catalysis

Publikationsverlauf

Eingereicht: 23. August 2022

Angenommen nach Revision: 29. September 2022

Artikel online veröffentlicht:
03. November 2022

• References

• 1a The Handbook of Natural Flavonoids, Vol. 1 and 2. Harborne JB, Baxter H. John Wiley & Sons; Chichester: 1999
• 1b Flavonoids: Chemistry, Biochemistry, and Applications . Anderson ØM, Markham KR. CRC Press; Boca Raton: 2006
• 1c Martens S, Mithöfer A. Phytochemistry 2005; 66: 2399
• 1d Verma AK, Pratap R. Tetrahedron 2012; 68: 8523
• 2a Middleton E, Kandaswani C, Theoharides TC. Pharmacol. Rev. 2000; 52: 673
• 2b Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chem. Rev. 2014; 114: 4960
• 2c Singh M, Kaur M, Silakari O. Eur. J. Med. Chem. 2014; 84: 206
• 2d Prasad S, Phromnoi K, Yadav VR, Chaturvedi MM, Aggarwal BB. Planta Med. 2010; 76: 1044
• 2e Beyer G, Melzig MF. Planta Med. 2003; 69: 1125
• 2f Verma AK, Pratap R. Nat. Prod. Rep. 2010; 27: 1571
• 2g Rocha-Pereira J, Cunha R, Pinto DC. G. A, Silva AM. S, Nascimento MS. J. Bioorg. Med. Chem. 2010; 18: 4195
• 3a Kshatriya R, Jejurkar VP, Saha S. Tetrahedron 2018; 74: 811
• 3b Santos CM. M, Silva AM. S. Eur. J. Org. Chem. 2017; 3115
• 3c Sun D.-W, Zhou Y.-Y, Jiang M, Nian T, Liu J.-T. Tetrahedron 2021; 91: 132226
• 4a Baker W. J. Chem. Soc. 1933; 1381
• 4b Mahal HS, Venkataraman K. J. Chem. Soc. 1934; 1767
• 4c Reddy BP, Krupadanam GL. D. J. Heterocycl. Chem. 1996; 33: 1561
• 4d Kalinin AV, Snieckus V. Tetrahedron Lett. 1998; 39: 4999
• 4e Thasana N, Ruchirawat S. Tetrahedron Lett. 2002; 43: 4515
• 4f Müller E, Kálai T, Jekö J, Hideg K. Synthesis 2000; 1415
• 4g Santos CM. M, Silva AM. S, Cavaleiro JA. S. Eur. J. Org. Chem. 2003; 4575
• 5a Allan J, Robinson R. J. Chem. Soc. Trans. 1924; 125: 2192
• 5b Dyke SF, Ollis WD, Sainsbury M. J. Org. Chem. 1961; 26: 2453
• 5c Looker JH, McMechan JH, Mader JW. J. Org. Chem. 1978; 43: 2344
• 6a Banerji A, Goomer NC. Synthesis 1980; 874
• 6b Hirao I, Yamaguchi M, Hamada M. Synthesis 1984; 1076
• 7a Jaen JC, Wise LD, Heffner TG, Pugsley TA, Meltzer LT. J. Med. Chem. 1991; 34: 248
• 7b Bolós J, Gubert S, Anglada L, Planas JM, Burgarolas C, Castelló JM, Sacristán A, Ortiz JA. J. Med. Chem. 1996; 39: 2962
• 7c Lubbe M, Appel B, Flemming A, Fischer C, Langer P. Tetrahedron 2006; 62: 11755
• 8a Nohara A, Umetani T, Sanno Y. Tetrahedron Lett. 1973; 14: 1995
• 8b Nohara A, Umetani T, Sanno Y. Tetrahedron Lett. 1974; 30: 3553
• 8c Sabitha G. Aldrichimica Acta 1996; 29: 13
• 9a Ellis GP, Barker G. Prog. Med. Chem. 1973; 9: 65
• 9b Costantino L, Rastelli G, Gamberini MC, Vinson JA, Bose P, Iannone A, Staffieri M, Antolini L, Del Corso A, Mura U, Albasini A. J. Med. Chem. 1999; 42: 1881
• 9c Fillion E, Dumas AM, Kuropatwa BA, Malhotra NR, Sitler TC. J. Org. Chem. 2006; 71: 409
• 10a Nixon NS, Scheinmann F, Suschitzky JL. Tetrahedron Lett. 1983; 24: 597
• 10b Kumar P, Bodas MS. Org. Lett. 2000; 2: 3821
• 11a Vedachalam S, Zeng J, Gorityala BK, Antonio M, Liu X.-W. Org. Lett. 2010; 12: 352
• 11b Vedachalam S, Wong Q.-L, Maji R, Zeng J, Ma J, Liu X.-W. Adv. Synth. Catal. 2011; 353: 219
• 11c Yoshida M, Fujino Y, Saito K, Doi T. Tetrahedron 2011; 67: 9993
• 11d Wen S.-S, Wang J, Luo Y.-M, Yang H. Tetrahedron 2014; 70: 9314
• 11e Stanek F, Stodulski M. Tetrahedron Lett. 2016; 57: 3841
• 12a Zhao J, Zhao Y, Fu H. Angew. Chem. Int. Ed. 2011; 50: 3769
• 12b Zhao J, Zhao Y, Fu H. Org. Lett. 2012; 14: 2710
• 13a Yatabe T, Jin X, Yamaguchi K, Mizuno N. Angew. Chem. Int. Ed. 2015; 54: 13302
• 13b Baruah S, Kaishap PP, Gogoi S. Chem. Commun. 2016; 52: 13004
• 13c Yue Y, Peng J, Wang D, Bian Y, Sun P, Chen C. J. Org. Chem. 2017; 82: 5481
• 13d Chang M.-Y, Tsai M.-C, Lin C.-Y. RSC Adv. 2021; 11: 11655
• 13e Zhang Y.-Y, Li H, Jiang X, Reddy CV. S, Liang H, Zhang Y, Cao R, Sun RW.-Y, Tse MK, Qiu L. Adv. Synth. Catal. 2022; 364: 525
• 14a Sashidhara KV, Kumar M, Kumar A. Tetrahedron Lett. 2012; 53: 2355
• 14b Narayan R, Antonchick AP. Chem. Eur. J. 2014; 20: 4568
• 15a Wang N, Cai S, Zhou C, Lu P, Wang Y. Tetrahedron 2013; 69: 647
• 15b Zhang S, Wan C, Wang Q, Zhang B, Gao L, Zha Z, Wang Z. Eur. J. Org. Chem. 2013; 2080
• 15c Wang X, Cheng G, Cui X. Chem. Commun. 2014; 50: 652
• 15d Zhao Y, Wang Z.-T, Cheng Y. Adv. Synth. Catal. 2014; 356: 2580
• 15e Wang P, Li Z, Cao S, Rao H. RSC Adv. 2015; 5: 106350
• 16a Wu X.-F, Neumann H, Beller M. Chem. Soc. Rev. 2011; 40: 4986
• 16b Wu X.-F, Neumann H, Beller M. Chem. Rev. 2013; 113: 1
• 16c Wu X.-F, Neumann H. ChemCatChem 2012; 4: 447
• 16d Ryu I, Sonoda N. Angew. Chem. Int. Ed. 1996; 35: 1050
• 16e Shen C, Wu X.-F. Chem. Eur. J. 2017; 23: 2973
• 16f Liu Q, Zhang H, Lei A. Angew. Chem. Int. Ed. 2011; 50: 10788
• 16g Wu L, Fang X, Liu Q, Jackstell R, Beller M, Wu X.-F. ACS Catal. 2014; 4: 2977
• 16h Li Y, Hu Y, Wu X.-F. Chem. Soc. Rev. 2018; 47: 172
• 16i Peng JB, Wu FP, Wu X.-F. Chem. Rev. 2019; 119: 2090
• 17a D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
• 17b Merkul E, Oeser T, Müller TJ. J. Chem. Eur. J. 2009; 15: 5006
• 17c Willy B, Müller TJ. J. Curr. Org. Chem. 2009; 13: 1777
• 17d Natte K, Chen J, Li H, Neumann H, Beller M, Wu XF. Chem. Eur. J. 2014; 20: 14184
• 17e Li H, Li W, Spannenberg A, Baumann W, Neumann H, Beller M, Wu XF. Chem. Eur. J. 2014; 20: 8541
• 17f Torres GM, Quesnel JS, Bijou D, Arndtsen BA. J. Am. Chem. Soc. 2016; 138: 7315
• 18a Miao H, Yang Z. Org. Lett. 2000; 2: 1765
• 18b Awuah E, Capretta A. Org. Lett. 2009; 11: 3210
• 18c Yang Q, Alper H. J. Org. Chem. 2010; 75: 948
• 18d Liang B, Huang M, You Z, Xiong Z, Lu K, Lu R, Fathi R, Chen J, Yang Z. J. Org. Chem. 2005; 70: 6097
• 18e Xue L, Shi L, Han Y, Xia C, Huynh HV, Li F. Dalton Trans. 2011; 40: 7632
• 18f Mansour W, Fettouhi M, Ali BE. ACS Omega 2020; 5: 32515
• 19a Wu X.-F, Neumann H, Beller M. Chem. Eur. J. 2012; 18: 12595
• 19b Zhu F, Wang Z, Li Y, Wu X.-F. Chem. Eur. J. 2017; 23: 3276
• 20 Zhu F, Li Y, Wang Z, Wu X.-F. Catal. Sci. Technol. 2016; 6: 2905
• 21 Lei Y, Li Z, Wan Y, Zhou X.-Y, Li G, Shi K. Appl. Organomet. Chem. 2018; 32: e4163
• 22a Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS. Nature 1992; 359: 710
• 22b Corma A. Top. Catal. 1997; 4: 249
• 22c Martin-Aranda RM, Cejka J. Top. Catal. 2010; 53: 141
• 23a Mehnert PC, Weaver DW, Ying JY. J. Am. Chem. Soc. 1998; 120: 12289
• 23b Mukhopadhyay K, Sarkar BR, Chaudhari RV. J. Am. Chem. Soc. 2002; 124: 9692
• 23c Gonzalez-Arellano C, Corma A, Iglesias M, Sanchez F. Adv. Synth. Catal. 2004; 346: 1758
• 23d Djakovitch L, Dufaud V, Zaidi R. Adv. Synth. Catal. 2006; 348: 715
• 23e Tsai F.-Y, Lin B.-N, Chen M.-J, Mou C.-Y, Liu S.-T. Tetrahedron 2007; 63: 4304
• 23f Li H, Chen J, Wan Y, Chai W, Zhang F, Lu Y. Green Chem. 2007; 9: 273
• 23g Cai M, Peng J, Hao W, Ding G. Green Chem. 2011; 13: 190
• 23h Wu W.-Y, Lin T.-C, Takahashi T, Tsai F.-Y, Mou C.-Y. ChemCatChem 2013; 5: 1011
• 23i Havasi F, Ghorbani-Choghamarani A, Nikpour F. New J. Chem. 2015; 39: 6504
• 23j Xu Z, Huang B, Zhou Z, Cai M. Synthesis 2020; 52: 581
• 24 Lempers HE. B, Sheldon RA. J. Catal. 1998; 175: 62
• 25 Posset T, Guenther J, Pope J, Oeser T, Blümel J. Chem. Commun. 2011; 47: 2059