Synthesis 2017; 49(24): 5364-5370
DOI: 10.1055/s-0036-1590895
paper
© Georg Thieme Verlag Stuttgart · New York

Recycled Pd/C-Catalyzed Heck Reaction of 2-Iodoanilines under Ligand-Free Conditions

Xiao-Yu Zhou*a, Xia Chen*a, Liang-Guang Wangb
  • aCollege of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui, 553004, P. R. of China   Email: zhouxiaoyu20062006@126.com
  • bCollege of Chemistry and Chemical Engineering, Anshun University, Anshun, 561000, P. R. of China
The work was supported by the Youth Science and Technology Talent Development Project in the Education Department of Guizhou Province (Grant No.qianjiaohe KY zi [2016] number 263) and by the Innovation Team of Liupanshui Normal University (Grant No. LPSSYKJTD201601).
Further Information

Publication History

Received: 27 June 2017

Accepted after revision: 07 August 2017

Publication Date:
28 August 2017 (eFirst)

Abstract

Recyclable Pd/C-catalyzed Heck reaction of 2-iodoanilines with acrylate has been developed. The reaction occurred readily in 1,4-dioxane using Pd/C (10 wt%) as catalyst under ligand-free conditions, and the cross-coupling products were obtained with medium to high yield. Gram-scale reactions and recycling of the catalyst were also demonstrated.

Supporting Information

 
  • References

  • 1 Cherney AH. Kadunce NT. Reisman SE. Chem. Rev. 2015; 115: 9587

    • For the application of Heck reaction, see:
    • 2a Tietze LF. Nobel T. Spescha M. J. Am. Chem. Soc. 1998; 120: 8971
    • 2b Dounay AB. Overman LE. Chem. Rev. 2003; 103: 2945
    • 2c Kwok TJ. Virgilio JA. Org. Process Res. Dev. 2005; 9: 694
    • 2d Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
    • 2e Martins A. Marquardt U. Kasravi N. Alberico D. Lautens M. J. Org. Chem. 2006; 71: 4937
    • 2f Cvetovich RJ. Reamer RA. DiMichele L. Chung JY. L. Chilenski JR. J. Org. Chem. 2006; 71: 8610
    • 2g Guthrie DB. Geib SJ. Curran DP. J. Am. Chem. Soc. 2009; 131: 15492
    • 2h Brovetto M. Gamenara D. Mendez PS. Seoane GA. Chem. Rev. 2011; 111: 4346
    • 2i Pires MJ. D. Poeira PD. L. Purificação SI. Marques MM. B. Org. Lett. 2016; 18: 3250
    • 2j Azcargorta AR. Coya E. Barbolla I. Lete E. Sotomayor N. Eur. J. Org. Chem. 2016; 2054
    • 2k Donatoni MC. Vieira YW. Brocksom TJ. Rabelo AC. Leite ER. de Oliveira KT. Tetrahedron Lett. 2016; 57: 3016
    • 2l Debnath S. Malakar S. Mondal S. Synthesis 2016; 48: 3544
    • 3a Gimbert C. Vallribera A. Org. Lett. 2009; 11: 269
    • 3b Omote M. Tanaka M. Tanaka M. Ikeda A. Tarui A. Sato K. Ando A. J. Org. Chem. 2013; 78: 6196
  • 4 Herrmann WA. Brossmer C. Ofele K. Reisinger C.-P. Priermeier T. Beller M. Fischer H. Angew. Chem., Int. Ed. Engl. 1995; 34: 1844
  • 5 Satyanarayana G. Helmchen G. Eur. J. Org. Chem. 2014; 2242
  • 6 Martinez R. Voica F. Genet J.-P. Darses S. Org. Lett. 2007; 9: 3213
  • 7 Liu C. Tang S. Liu D. Yuan J. Zheng L. Meng L. Lei A. Angew. Chem. Int. Ed. 2012; 51: 3638
  • 8 Nacci VC. A. Monopoli A. Ieva E. Cioffi N. Org. Lett. 2005; 7: 617
  • 9 Tian J. Moeller KD. Org. Lett. 2005; 7: 5381

    • For Heck reaction in green solvents, see:
    • 10a Carmichael AJ. Earle MJ. Holbrey JD. McCormac PB. Seddon KR. Org. Lett. 1999; 1: 997
    • 10b Vallin KS. A. Emilsson P. Larhed M. Hallberg A. J. Org. Chem. 2002; 67: 6243
    • 10c Selvakumar K. Zapf A. Beller M. Org. Lett. 2002; 4: 3031
    • 10d Chandrasekhar S. Narsihmulu C. Sultana SS. Reddy NR. Org. Lett. 2002; 4: 4399
    • 10e Mo J. Xu L. Xiao J. J. Am. Chem. Soc. 2005; 127: 751
    • 10f Li S. Lin Y. Xie H. Zhang S. Xu J. Org. Lett. 2006; 8: 391
    • 10g Xu H.-J. Zhao Y.-Q. Zhou X.-F. J. Org. Chem. 2011; 76: 8036

      For asymmetric Heck reactions, see:
    • 11a Lapierre AJ. B. Geib SJ. Curran DP. J. Am. Chem. Soc. 2007; 129: 494
    • 11b Oestreich M. Angew. Chem. Int. Ed. 2014; 53: 2282
    • 11c Yue G. Lei K. Hirao H. Zhou JS. Angew. Chem. Int. Ed. 2015; 54: 6531

      For oxidative Heck reactions, see:
    • 12a Beccalli EM. Broggini G. Martinelli M. Sottocornola S. Chem. Rev. 2007; 107: 5318
    • 12b Lipshutz BH. Taft BR. Org. Lett. 2008; 10: 1329
    • 12c Bras JL. Muzart J. Chem. Rev. 2011; 111: 1170
    • 12d He Z. Kirchberg S. Frçhlich R. Studer A. Angew. Chem. Int. Ed. 2012; 51: 3699
    • 12e Izawa Y. Zheng C. Stahl SS. Angew. Chem. Int. Ed. 2013; 52: 3672

      For the palladium catalysis system applied in Heck reactions, see:
    • 13a Littke AF. Fu GC. J. Am. Chem. Soc. 2001; 123: 6989
    • 13b Mino T. Shirae Y. Sasai Y. Sakamoto M. Fujita T. J. Org. Chem. 2006; 71: 6834
    • 13c Muthumari S. Mohan N. Ramesh R. Tetrahedron Lett. 2015; 56: 4170
    • 13d Sperger T. Stirner CK. Schoenebeck F. Synthesis 2017; 49: 115

      For Heck reaction under heterogeneous catalysis, see:
    • 14a Beletskaya IP. Cheprakov AV. Chem. Rev. 2000; 100: 3009
    • 14b Hajiwara H. Shimizu Y. Hoshi T. Suzuki T. Ando M. Ohkubo K. Yokoyama C. Tetrahedron Lett. 2001; 42: 4349
    • 14c Hamza K. Abu-Reziq R. Avnir D. Blum J. Org. Lett. 2004; 6: 925
    • 14d Perosa A. Tundo P. Selva M. Zinovyev S. Testa A. Org. Biomol. Chem. 2004; 2: 2249
    • 14e Xie X. Lu J. Chen B. Han J. She X. Pan X. Tetrahedron Lett. 2004; 45: 809
    • 14f Dahan A. Portnoy M. Org. Lett. 2005; 5: 1197
    • 14g Yin L. Liebscher J. Chem. Rev. 2007; 107: 133
    • 14h Jiang X. Sclafani J. Prasad K. Repic O. Blacklock TJ. Org. Process Res. Dev. 2007; 11: 769
    • 14i Lipshutz BH. Taft BR. Org. Lett. 2008; 10: 1329
    • 14j Schils D. Stappers F. Solberghe G. van Heck R. Coppens M. van den Heuvel D. van der Donck P. Callewaert T. Meeussen F. Org. Process Res. Dev. 2008; 12: 530
    • 14k Niembro S. Shafir A. Vallribera A. Alibes R. Org. Lett. 2008; 10: 3215
    • 14l Borja G. Monge-Marcet A. Pleixats R. Parella T. Cattoën X. Man MW. C. Eur. J. Org. Chem. 2012; 3625
    • 14m Liu W. Wang D. Duan Y. Zhang Y. Bian F. Tetrahedron Lett. 2015; 56: 1784