Synthesis 2019; 51(18): 3462-3470
DOI: 10.1055/s-0037-1611539
paper
© Georg Thieme Verlag Stuttgart · New York

Chemo- and Regioselective Palladium(II)-Catalyzed Aminoaryl­ation of N-Allylureas Providing 4-Arylmethyl Imidazolidinones

Sabrina Giofrè
a   DISFARM, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy   Email: egle.beccalli@unimi.it
,
a   DISFARM, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy   Email: egle.beccalli@unimi.it
,
Francesca Foschi
b   Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy
,
Concetta La Rosa
a   DISFARM, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy   Email: egle.beccalli@unimi.it
,
Leonardo Lo Presti
b   Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy
,
Michael S. Christodoulou
a   DISFARM, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy   Email: egle.beccalli@unimi.it
› Author Affiliations
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.
Further Information

Publication History

Received: 08 March 2019

Accepted after revision: 16 April 2019

Publication Date:
14 May 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.

Supporting Information

 
  • 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

      For selected examples of intramolecular oxidative Pd-catalyzed domino reactions on alkenes, see:
    • 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

    • For selected examples of analogous reactions on alkynes, see:
    • 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

    • For selected examples of analogous reactions on allenes, see:
    • 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
    • 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