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Synthesis 2019; 51(18): 3462-3470
DOI: 10.1055/s-0037-1611539
DOI: 10.1055/s-0037-1611539
paper
Chemo- and Regioselective Palladium(II)-Catalyzed Aminoarylation of N-Allylureas Providing 4-Arylmethyl Imidazolidinones
Università degli Studi di Milano is acknowledged for financial support. Support from European Cooperation in Science and Technology through CMST COST Action [CA15106 - C–H Activation in Organic Synthesis (CHAOS)] is also gratefully acknowledged.Weitere Informationen
Publikationsverlauf
Received: 08. März 2019
Accepted after revision: 16. April 2019
Publikationsdatum:
14. Mai 2019 (online)
Abstract
The aminoarylation reaction of N-allylureas under oxidative palladium catalysis, in the absence of ligands and by using inexpensive H2O2 as the sole oxidant, occurs in a chemo- and regioselective fashion. This intramolecular process takes place via a 5-exo-trig cyclization, and represents an easy approach to 4-arylmethyl imidazolidinones.
Key words
palladium catalysis - aminoarylation - hydrogen peroxide - imidazolidinones - ureas - domino reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611539.
- Supporting Information
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References
- 1a Tietze LF. Chem. Rev. 1996; 96: 115
- 1b Poli G, Giambastiani G, Heumann A. Tetrahedron 2000; 56: 5959
- 1c Pellissier H. Chem. Rev. 2013; 113: 442
- 1d Clavier H, Pellissier H. Adv. Synth. Catal. 2012; 354: 3347
- 1e Yin G, Mu X, Liu G. Acc. Chem. Res. 2016; 49: 2413
- 1f Vlaar T, Ruijter E, Orru VA. Adv. Synth. Catal. 2011; 353: 809
- 1g Jensen KH, Sigman MS. Org. Biomol. Chem. 2008; 6: 4083
- 2a Chen P.-Y, Huang K.-S, Tsai C.-C, Wang T.-P, Wang E.-C. Org. Lett. 2012; 14: 4930
- 2b Alonso F, Sanchez D, Soler T, Yus M. Adv. Synth. Catal. 2008; 350: 2118
- 2c Abbiati G, Beccalli EM, Broggini G, Martinelli M, Paladino G. Synlett 2006; 73
- 2d Szolcsanyi P, Gracza T. Chem. Commun. 2005; 3948
- 2e Alladoum J, Vrancken E, Mangeney P, Roland S, Kadouri-Puchot C. Org. Lett. 2009; 11: 3746
- 2f Asao N, Chan CS, Takahashi K, Yamamoto Y. Tetrahedron 2005; 61: 11322
- 2g Watanabe K, Iwata Y, Adachi S, Nishikawa T, Yoshida Y, Kameda S, Ide M, Saikawa Y, Nakata M. J. Org. Chem. 2010; 75: 5573
- 2h Gazzola S, Beccalli EM, Bernasconi A, Borelli T, Broggini G, Mazza A. Eur. J. Org. Chem. 2016; 4534
- 2i Le Bras J, Muzart J. Chem. Soc. Rev. 2014; 43: 3003
- 2j Alcaide B, Almendros P, Rodriguez-Acebes R. J. Org. Chem. 2006; 71: 2346
- 2k Beccalli EM, Bernasconi A, Borsini E, Broggini G, Rigamonti M, Zecchi G. J. Org. Chem. 2010; 75: 6923
- 3a Beccalli EM, Broggini G, Martinelli M, Sottocornola S. Chem. Rev. 2007; 107: 5318
- 3b Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 3c Beccalli EM, Broggini G, Gazzola S, Mazza A. Org. Biomol. Chem. 2014; 12: 6767
- 4a Yin G, Wu T, Liu G. Chem. Eur. J. 2012; 18: 451
- 4b Zhu H, Chen P, Liu G. Org. Lett. 2015; 17: 1485
- 4c Zhu H, Chen P, Liu G. J. Am. Chem. Soc. 2014; 136: 1766
- 4d Yin G, Liu G. Angew. Chem. Int. Ed. 2008; 47: 5442
- 5a Broggini G, Barbera V, Beccalli EM, Chiacchio U, Fasana A, Galli S, Gazzola S. Adv. Synth. Catal. 2013; 355: 1640
- 5b Broggini G, Beccalli EM, Borelli T, Brusa F, Gazzola S, Mazza A. Eur. J. Org. Chem. 2015; 4261
- 6 Gazzola S, Beccalli EM, Borelli T, Castellano C, Diamante D, Broggini G. Synlett 2018; 29: 503
- 7a Wang Z, Luo W, Lu L, Yin B. J. Org. Chem. 2018; 83: 10080
- 7b Arcadi A, Cacchi S, Fabrizi G, Ghirga F, Goggiamani A, Iazzetti A, Marinelli F. Synthesis 2018; 50: 1133
- 7c Yang M.-N, Yan D.-M, Zhao Q.-Q, Chen J.-R, Xiao W.-J. Org. Lett. 2017; 19: 5208
- 7d Wu L, Meng Y, Ferguson J, Wang L, Zeng F. J. Org. Chem. 2017; 82: 4121
- 7e Yu R, Li D, Zeng F. J. Org. Chem. 2018; 83: 323
- 7f Zhang W, Chen P, Liu G. Angew. Chem. Int. Ed. 2017; 56: 5336
- 7g Bao X, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2017; 56: 9577
- 7h Yang H.-B, Pathipati SR, Selander N. ACS Catal. 2017; 7: 8441
- 7i Zheng J, Huang L, Huang C, Wu W, Jiang H. J. Org. Chem. 2015; 80: 1235
- 7j Faulkner A, Scott JS, Bower JF. J. Am. Chem. Soc. 2015; 137: 7224
- 7k Bao H, Bayeh L, Tambar UK. Chem. Sci. 2014; 5: 4863
- 7l Hewitt JF. M, Williams L, Aggarwal P, Smith CD, France DJ. Chem. Sci. 2013; 4: 3538
- 7m Schultz DM, Wolfe JP. Synthesis 2012; 44: 351
- 7n Jiang C, Covell DJ, Stepan AF, Plummer MS, White MC. Org. Lett. 2012; 14: 1386
- 7o Brenzovich WE. Jr, Benitez D, Lackner AD, Shunatona HP, Tkatchouk E, Goddard WA. III, Toste FD. Angew. Chem. Int. Ed. 2010; 49: 5519
- 7p Fritz JA, Wolfe JP. Tetrahedron 2008; 64: 6838
- 7q Tamaru Y, Hojo M, Kawamura S, Yoshida Z. J. Org. Chem. 1986; 51: 4089
- 7r Zhang L, Dong C, Ding C, Chen J, Tang W, Li H, Xu L, Xiao J. Adv. Synth. Catal. 2013; 355: 1570
- 7s Trejos A, Fardost A, Yahiaoui S, Larhed M. Chem. Commun. 2009; 7587
- 8a Rao W.-H, Yin X.-S, Shi B.-F. Org. Lett. 2015; 17: 3758
- 8b Gazzola S, Beccalli EM, Borelli T, Castellano C, Chiacchio MA, Diamante D, Broggini G. J. Org. Chem. 2015; 80: 7226
- 8c Strambeanu II, White MC. J. Am. Chem. Soc. 2013; 137: 12032
- 8d Muniz K, Iglesias A, Fang Y. Chem. Commun. 2009; 5591
- 8e Gimeno A, Cuenca AB, Médio-Simon M, Asensio G. Adv. Synth Catal. 2014; 356: 229
- 8f Li H, Widenhoefer A. Tetrahedron 2010; 66: 4827
- 8g Cochran BM, Micheal FE. Org. Lett. 2008; 10: 5039
- 9a Rahbæk L, Christophersen C. J. Nat. Prod. 1997; 60: 175
- 9b Sheppeck JE. II, Gilmore JL, Tebben A, Xue C.-B, Liu R.-Q, Decicco CP, Duan JJ.-W. Bioorg. Med. Chem. Lett. 2007; 17: 2769
- 9c Batra S, Tusi Z, Madapa S. Anti-Infective Agents Med. Chem. 2006; 5: 135
- 9d Bronson JJ, DenBleyker KL, Falk PL, Mate RA, Ho H.-T, Pucci MJ, Snyder LB. Bioorg. Med. Chem. Lett. 2003; 13: 873
- 9e Congiu C, Cocco MT, Onnis V. Bioorg. Med. Chem. Lett. 2008; 18: 989
- 9f Watanabe K, Morinaka Y, Hayashi Y, Shinoda M, Nishi H, Fukushima N, Watanabe T, Ishibashi A, Yuki S, Tanaka M. Bioorg. Med. Chem. Lett. 2008; 18: 1478
- 9g Xue N, Yang X, Wu R, Chen J, He Q, Yang B, Lu X, Hu Y. Bioorg. Med. Chem. 2008; 16: 2550
- 10a Alexanian EJ, Lee C, Sorensen EJ. J. Am. Chem. Soc. 2005; 127: 7690
- 10b Sibbald PA, Michael FE. Org. Lett. 2009; 11: 1147
- 11a Qi X, Chen C, Hou C, Fu L, Chen P, Liu G. J. Am. Chem. Soc. 2018; 140: 7415
- 11b Chen C, Chen P, Liu G. J. Am. Chem. Soc. 2015; 137: 15648
- 11c Mancheno DE, Thornton AR, Stoll AH, Kong A, Blakey SB. Org. Lett. 2010; 12: 4110
- 12 CCDC 1896769 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 13 Balko TW, Brinkmeyer RS, Terando NH. Tetrahedron Lett. 1989; 30: 2045
- 14 Li D, Mao T, Huang J, Zhu Q. Chem. Commun. 2017; 53: 3450
- 15 Bruker AXS Inc., SAINT+, Madison, Wisconsin, USA, 2012.
- 16 Bruker AXS Inc., SADABS, Madison, Wisconsin, USA, 2001.
- 17 Palatinus L, Chapuis G. J. Appl. Crystallogr. 2007; 40: 786
- 18 Sheldrick GM. Acta Crystallogr. 2015; 71: 3-8
For selected examples of intramolecular oxidative Pd-catalyzed domino reactions on alkenes, see:
For selected examples of analogous reactions on alkynes, see:
For selected examples of analogous reactions on allenes, see: