Abstract
The necessity of a catalyst in the Petasis-Borono Mannich multicomponent reaction was studied. Besides the catalyst-free reaction, monometallic and bimetallic catalysts were tested on different supports with various metal loadings. It was concluded that a 4 Å molecular sieve-supported copper catalyst with low (1.2 wt%) copper content accelerated the coupling the most.
Graphical abstract
Similar content being viewed by others
References
Miyaura N, Yamada K, Suzuki A (1979) Tetrahedron Lett 20:3437
Chan DMT, Monaco KL, Wang RP, Winters MP (1998) Tetrahedron Lett 39:2933
Petasis NA, Akritopoulou I (1993) Tetrahedron Lett 34:583
McLean NJ, Tye H, Whittaker M (2004) Tetrahedron Lett 45:993
Mandai H, Murota K, Sakai T (2010) Tetrahedron Lett 51:4779
Mandai H, Murota K, Suga S (2012) Heterocycles 85:1655
Yu A, Wu Y, Cheng B, Wei K, Li J (2009) Adv Synth Catal 351:767
Frauenlob R, García C, Bradshaw GA, Burke HM, Bergin E (2012) J Org Chem 77:4445
Shi X, Hebrault D, Humora M, Kiesman WF, Peng H, Talreja T, Wang Z, Xin Z (2012) J Org Chem 77:1154
Souza RY, Bataglion GA, Ferreira DAC, Gatto CC, Eberlin MN, Neto BAD (2015) RSC Adv 5:76337
Candeias NR, Montalbano F, Cal PMSD, Gois PMP (2010) Chem Rev 110:6169
Candeias NR, Cal PMSD, André V, Duarte MT, Veiros LF, Gois PMP (2010) Tetrahedron 66:2736
Beenen MA, Weix DJ, Ellman JA (2006) J Am Chem Soc 128:6304
Kiss Á, Németh J, Fodor A, Hell Z (2015) Period Polytech. Chem Eng 59:72
Fodor A, Hell Z, Pirault-Roy L (2014) Appl Catal A 484:39
Fodor A, Magyar Á, Barczikai D, Pirault-Roy L, Hell Z (2015) Catal Lett 145:834
Fodor A, Hell Z, Pirault-Roy L (2016) Catal Lett. doi:10.1007/s10562-015-1673-6
Katritzky AR, Abdel-Fattah AAA, Tymoshenko DO, Belyakov SA, Ghiviriga I, Steel PJ (1999) J Org Chem 64:6071
Acknowledgments
Anna Fodor is grateful to the fellowship of the Pro Progressio foundation.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Fodor, A., Hell, Z. & Pirault-Roy, L. Catalytic activity of metal-doped porous materials in the salicylaldehyde Petasis-Borono Mannich reaction. Monatsh Chem 147, 749–753 (2016). https://doi.org/10.1007/s00706-016-1681-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-016-1681-2