Abstract: Homogenous catalysis is a powerful tool for organic synthesis but its success in industrial application is limited because of difficult catalyst separation and reuse. To overcome these issues, the use of biphasic catalysis is at present of great interest because the catalyst is confined in one of the two-phases and the product in the other phase allowing for a prompt recovery of the product and an easy recycle of the catalyst. In particular, the development of water soluble catalysts for aqueous/organic biphasic reactions is increasingly attractive [1]. Our research group has been involved in the synthesis of triazolyl ligands by taking advantage of the copper-catalyzed azide-alkyne [3+2] cyclization [2]. Recently, we have synthesized a small library of N-N or N-S ligands which have been employed in Suzuki-Miyaura reactions [3,4]. In this work, we wish to present our studies on biphasic (water/toluene) catalytic hydrogenation of C=O and C=C (Schemes 3 & 4) double bonds using a water soluble triazole ligand in combination with Ruthenium and Iridium. [1] (a) Cornils B.; Herrmann W. A.; Horvath I. T.; Leitner W.; Mecking S.; Olivier-Bourbigou H.; Vogt (Eds.) D. Multiphase Homogeneous Catalysis, Wiley-VCH, Weinheim, 2005. (b) Joo F. Aqueous Organometallic Catalysis, Kluwer Acad. Publ. Dordrecht, 2001. [2] V. V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem., Int. Ed. 2002, 41, 2596. [3] Amadio E.; Scrivanti A.; Chessa G.; Matteoli U.; Beghetto V.; Bertoldini M.; Rancan M.; Venzo A.; Bertani R. J. Org. Chem. 2012, 716, 193. [4] Amadio E.; Bertoldini M.; Scrivanti A.; Chessa G.; Beghetto V.; Matteoli U.; Bertani R.; Dolmella A. Inorg. Chim. Acta 2011, 370, 388.
Synthesis of Water-soluble Triazole Ligands and Application of Their Metal Complexes in Biphasic Hydrogenations of C=C and C=O
ALAM, MD MAHBUBUL;PAGANELLI, Stefano;BEGHETTO, Valentina;SCRIVANTI, Alberto;AMADIO, Emanuele;BERTOLDINI, Matteo;MATTEOLI, Ugo
2014-01-01
Abstract
Abstract: Homogenous catalysis is a powerful tool for organic synthesis but its success in industrial application is limited because of difficult catalyst separation and reuse. To overcome these issues, the use of biphasic catalysis is at present of great interest because the catalyst is confined in one of the two-phases and the product in the other phase allowing for a prompt recovery of the product and an easy recycle of the catalyst. In particular, the development of water soluble catalysts for aqueous/organic biphasic reactions is increasingly attractive [1]. Our research group has been involved in the synthesis of triazolyl ligands by taking advantage of the copper-catalyzed azide-alkyne [3+2] cyclization [2]. Recently, we have synthesized a small library of N-N or N-S ligands which have been employed in Suzuki-Miyaura reactions [3,4]. In this work, we wish to present our studies on biphasic (water/toluene) catalytic hydrogenation of C=O and C=C (Schemes 3 & 4) double bonds using a water soluble triazole ligand in combination with Ruthenium and Iridium. [1] (a) Cornils B.; Herrmann W. A.; Horvath I. T.; Leitner W.; Mecking S.; Olivier-Bourbigou H.; Vogt (Eds.) D. Multiphase Homogeneous Catalysis, Wiley-VCH, Weinheim, 2005. (b) Joo F. Aqueous Organometallic Catalysis, Kluwer Acad. Publ. Dordrecht, 2001. [2] V. V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem., Int. Ed. 2002, 41, 2596. [3] Amadio E.; Scrivanti A.; Chessa G.; Matteoli U.; Beghetto V.; Bertoldini M.; Rancan M.; Venzo A.; Bertani R. J. Org. Chem. 2012, 716, 193. [4] Amadio E.; Bertoldini M.; Scrivanti A.; Chessa G.; Beghetto V.; Matteoli U.; Bertani R.; Dolmella A. Inorg. Chim. Acta 2011, 370, 388.
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