Synthesis 2018; 50(07): 1521-1526
DOI: 10.1055/s-0037-1609152
paper
© Georg Thieme Verlag Stuttgart · New York

Aminocarbonylation of N-Containing Heterocycles with Aromatic Amines Using Mo(CO)6

Marius Mamone
a   Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405 Orsay, France
,
Jessy Aziz
a   Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405 Orsay, France
,
Julie Le Bescont
a   Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405 Orsay, France
b   Université Paris Sud, Université Paris-Saclay, 91405 Orsay, France   Email: sandrine.piguel@u-psud.fr
,
Sandrine Piguel*
a   Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405 Orsay, France
b   Université Paris Sud, Université Paris-Saclay, 91405 Orsay, France   Email: sandrine.piguel@u-psud.fr
› Author Affiliations
French program ‘Investissement d’Avenir – Institut Carnot’ managed by the National Research Agency (ANR-11-CARN-008-01).
Further Information

Publication History

Received: 13 December 2017

Accepted after revision: 13 December 2017

Publication Date:
18 January 2018 (online)


Abstract

We describe herein the palladium-catalyzed aminocarbonylation of nitrogen-containing heterocycles with aniline derivatives using molybdenum hexacarbonyl as a CO solid source, expanding the scope of the limited examples. This method is compatible with a variety of substitutions on the aniline moiety. The simple reaction conditions include easily available Pd(dppf)Cl2 catalyst, DBU as base in DMF at 120 °C for 3 hours in sealed tube thereby leading to the isolation of 21 compounds with yields ranging from 18 to 82%. We also show that double aminocarbonylation reactions are possible in satisfactory yields regarding both coupling partners.

Supporting Information

 
  • References

    • 1a The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Material Science . Greenberg A. Breneman CM. Liebman JF. Wiley-Interscience; New York: 2000
    • 1b Humphrey JM. Chamberlin AR. Chem. Rev. 1997; 97: 2243
    • 2a Valeur E. Bradley M. Chem. Soc. Rev. 2009; 38: 606
    • 2b Chaudhari PS. Salim SD. Sawant RV. Akamanchi KG. Green Chem. 2010; 12: 1707
    • 2c Lundberg H. Tinnis F. Selander N. Hadolfsson H. Chem. Soc. Rev. 2014; 43: 2714

      For selected reviews:
    • 3a Roy S. Roy S. Gribble GW. Tetrahedron 2012; 68: 9867
    • 3b Ojeda-Porras A. Gamba-Sanchez D. J. Org. Chem. 2016; 81: 11548
    • 3c de Figueiredo RM. Suppo JS. Campagne JM. Chem. Rev. 2016; 116: 12029
    • 4a Schoenberg A. Heck RF. J. Org. Chem. 1974; 39: 3327
    • 4b Brennführer A. Neumann H. Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
    • 5a Friis SD. Skyrdstrup T. Buchwald SL. Org. Lett. 2014; 16: 4296
    • 5b Lei Y. Xiao S. Li G. Gu Y. Wu H. Shi K. Appl. Organomet. Chem. 2016; 1
  • 6 Takacs A. Jakab B. Petz A. Kollar L. Tetrahedron 2007; 63: 10372
  • 8 Tambade PJ. Patil YP. Bhanushali MJ. Bhanage BM. Synthesis 2008; 2347
  • 9 Kaiser N.-FK. Hallberg A. Larhed M. J. Comb. Chem. 2002; 4: 109
  • 10 Wannberg J. Larhed M. J. Org. Chem. 2003; 68: 5750

    • For recent work:
    • 11a Odell LR. Russo F. Larhed M. Synlett 2012; 23: 685
    • 11b Mane RS. Sasaki T. Bhanage BM. RSC Adv. 2015; 5: 94776
    • 11c Hajipour A.-R. Tavangar-Rizi Z. Iranpoor N. RSC Adv. 2016; 6: 78468
    • 11d Bordessa A. Ferry A. Lubin-Germain N. J. Org. Chem. 2016; 81: 12459
    • 11e Wang Z. Yin Z. Wu X.-F. Chem. Eur. J. 2017; 23: 15026
  • 12 Letavic MA. Ly KS. Tetrahedron Lett. 2007; 48: 2339
  • 13 Begouin A. Queiroz M.-JR. P. Eur. J. Org. Chem. 2009; 2820
  • 14 Iranpoor N. Firouzabadi H. Motevalli S. Talebi M. Tetrahedron 2013; 69: 418
  • 15 Wu X.-F. Oschatz S. Sharif M. Beller M. Langer P. Tetrahedron 2014; 70: 23
  • 16 Xu T. Alper H. J. Am. Chem. Soc. 2014; 136: 16970
  • 17 Fors BP. Dooleweerdt K. Zeng Q. Buchwald SL. Tetrahedron 2009; 65: 6576
  • 18 Holsworth D. Waaler J. Machon O. Krauss S. WO 2010139966, 2010
  • 19 Fang W. Deng Q. Xu M. Tu T. Org. Lett. 2013; 15: 3678
  • 20 Nammalwar B. Muddala NP. Watts FM. Bunce RA. Tetrahedron 2015; 71: 9101
  • 21 Kumar KN. Sreeramamurthy K. Palle S. Mukkanti K. Das P. Tetrahedron Lett. 2010; 51: 899
  • 22 Crawford SM. Lavery CB. Stradiotto M. Chem. Eur. J. 2013; 19: 16760
  • 23 Jarak I. Pavlovic G. Karminski-Zamola G. Struct. Chem. 2007; 18: 103
  • 24 Rossi SA. Shimkin KW. Xu Q. Mori-Quiroz LM. Watson DA. Org. Lett. 2013; 15: 2314
  • 25 Nicolas L. Angibaud P. Stansfield I. Meerpoel L. Reymond S. Cossy J. RSC Adv. 2013; 3: 18787