Potential applications of Zr-KIT-5: Hantzsch reaction,
Meerwein–Ponndorf–Verley (MPV) reduction of 4-tert-
butylcyclohexanone, and Prins reaction of citronellal
Vinju Vasudevan Srinivasan
Received: 13 January 2015 / Accepted: 27 June 2015 / Published online: 11 July 2015
Ó The Author(s) 2015. This article is published with open access at Springerlink.com
Abstract The acidity of Zr-incorporated large pore cubic mesoporous silicate,
KIT-5, with Fm3m symmetry was explored as catalyst in the Hantzsch reaction for
preparation of 1,4-dihydropyridine (DHP) derivatives, Meerwein–Ponndorf–Verley
(MPV) reduction of 4-tert-butylcyclohexanone, and Prins reaction of citronellal.
The catalyst showed *82–94 % selectivity for formation of DHP derivatives based
on substituted benzaldehydes. For the intramolecular cyclization of citronellal, the
activity and isomer selectivity increased with Zr content. Both these reactions
proceeded to nearly total conversion in relatively short reaction times of 3 h and
30 min, respectively. In sharp contrast, MPV reduction of 4-tert-butylcyclohex-
anone yielded 95 % conversion in 4 days, similar to those reported for Zr-TUD-1.
Keywords Zr-KIT-5 Á Hantzsch reaction Á Isopulegol Á Prins reaction Á MPV
Vinju Vasudevan Srinivasan and Adeline Ranoux have contributed equally to the present work.
Electronic supplementary material The online version of this article (doi:10.1007/s11164-015-2157-4)
contains supplementary material, which is available to authorized users.
& Ulf Hanefeld
& Anand Ramanathan
Department of Chemistry, Anna University, Chennai 600025, India
Center for Environmentally Beneﬁcial Catalysis, The University of Kansas, Lawrence,
KS 66047, USA
Gebouw voor Scheikunde, Technische Universiteit Delft, Julianalaan 136,
2628 BL Delft, The Netherlands
Res Chem Intermed (2016) 42:2399–2408