Abstract
An efficient route for the catalytic synthesis of aryl amides via the aminocarbonylation of aryl iodides with amines is described using palladium supported on triphenylphosphine-functionalized porous organic polymer (Pd@KAPs(Ph-PPh3)) as the catalyst. Under low carbon monoxide pressure, the catalyst exhibited remarkable activity, and only 0.5 mol% palladium loading was required to achieve moderate to excellent yields (70–97 %) of aryl amides. The catalyst can be easily separated by a simple filtration process and recycled up to seven times with only minor loss of activity. The salient features of this protocol are the simplicity in handling of catalyst, low CO pressure, good functional group tolerance, high catalytic activity, negligible palladium leaching and effective catalyst recyclability.
Similar content being viewed by others
References
Pattabiraman VR, Bode JW (2011) Nature 480:471
Zhang DW, Zhao X, Hou JL, Li ZT (2012) Chem Rev 112:5271
Gadge ST, Bhanage BM (2014) RSC Adv 4:10367
Sumino S, Fusano A, Fukuyama T, Ryu I (2014) Acc Chem Res 47:1563
Wu X-F, Neumann H, Beller M (2013) Chem Rev 113:1
Omae I (2011) Coord Chem Rev 255:139
Wu X-F, Neumann H, Beller M (2011) Chem Soc Rev 40:4986
Xu T, Alper H (2014) J Am Chem Soc 136:16970
Quesnel JS, Arndtsen BA (2013) J Am Chem Soc 135:16841
Fang T, Gao X-H, Tang R-Y, Zhang X-G, Deng C-L (2014) Chem Commun 50:14775
Gadge ST, Bhanage BM (2014) Org Biomol Chem 12:5727
Xu T, Alper H (2013) Tetrahedron Lett 54:5496
Tinnis F, Verho O, Gustafson KPJ, Tai C-W, Bäckvall J-E, Adolfsson H (2014) Chem Eur J 20:5885
Cai M, Zhao H, Huang Y (2005) J Mol Catal A Chem 238:41
Hao WY, Sha JC, Sheng SR, Cai MZ (2008) Catal Commun 10:257
Dang TT, Zhu Y, Ghosh SC, Chen A, Chai CLL, Seayad AM (2012) Chem Commun 48:1805
Dang TT, Zhu Y, Ngiam JSY, Ghosh SC, Chen A, Seayad AM (2013) ACS Catal 3:1406
Qureshi ZS, Revankar SA, Khedkar MV, Bhanage BM (2012) Catal Today 198:148
Islam SM, Ghosh K, Roy AS, Molla RA (2014) RSC Adv 4:38986
Molla RA, Iqubal MA, Ghosh K, Roy AS, Islam SM (2014) RSC Adv 4:48177
Li B, Guan Z, Wang W, Yang X, Hu J, Tan B, Li T (2012) Adv Mater 24:3390
Sun Q, Jiang M, Shen Z, Jin Y, Pan S, Wang L, Meng X, Chen W, Ding Y, Li J, Xiao F-S (2014) Chem Commun 50:11844
Rose M (2014) ChemCatChem 6:1166
Zhang Q, Yang Y, Zhang S (2013) Chem Eur J 19:10024
Jiang M, Yan L, Ding Y, Sun Q, Liu J, Zhu H, Lin R, Xiao F, Jiang Z, Liu J (2015) J Mol Catal A Chem 404–405:211
Sun Q, Dai Z, Liu X, Sheng N, Deng F, Meng X, Xiao F-S (2015) J Am Chem Soc 137:5204
Lei Y, Wu L, Zhang X, Mei H, Gu Y, Li G (2015) J Mol Catal A Chem 398:164
Mei H, Hu J, Xiao S, Lei Y, Li G (2014) Appl Catal A Gen 475:40
Mei H, Xiao S, Zhu T, Lei Y, Li G (2014) Transit Met Chem 39:443
Barnard CFJ (2008) Org Process Res Dev 12:566
Genelot M, Villandier N, Bendjeriou A, Jaithong P, Djakovitch L, Dufaud V (2012) Catal Sci Technol 2:1886
Balogh J, Kuik Á, Ürge L, Darvas F, Bakos J, Skoda-Földes R (2009) J Mol Catal A Chem 302:76
Takács E, Varga C, Skoda-Földes R, Kollár L (2007) Tetrahedron Lett 48:2453
Papp M, Skoda-Földes R (2013) J Mol Catal A Chem 378:193
Acknowledgments
This work is partly supported financially by the 863 Program of Ministry of Science and Technology of China (NC2010 MA0137). The authors thank for financial support from the National Natural Science Foundation of China (51504134), Guizhou “125 Plan” Key Project of Science and Technology Project [Qian jiao he zhong da zhuang xiang zi (2013) 026] and Liupanshui normal university creative team (LPSSYKJTD201401).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Lei, Y., Zhang, X., Gu, Y. et al. Palladium supported on triphenylphosphine-functionalized porous organic polymer: an efficient heterogeneous catalyst for aminocarbonylation. Transition Met Chem 41, 1–7 (2016). https://doi.org/10.1007/s11243-015-9990-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-015-9990-6