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N-heterocyclic carbenes (NHCs) for (Organo-) Catalysis

Several different projects entail the use of tailored N-heterocyclic carbenes (NHCs) for use in polymerization reactions. Taking advantage of their high basicity and pronounced nucleophilic character, NHCs can also be protected by different means, e.g., by the addition of CO2 or by suitable transition metal ions[1]. The thus prepared systems then serve as latent catalysts that can be activated by application of heat: for the synthesis of poly(urethane)s or poly(amide)s via reaction injection molding of one-component systems[2-3], or for the polymerization of lactones or acrylates[4-5]. Based on this principle, it is also possible to create fully air-stable and latent single-component curing systems for epoxy resins for use in the preparation of advanced composite materials[6]. Complementary, the novel NHCs are used for the synthesis of the corresponding transition metal-NHC complexes, which serve as excellent catalysts for C-C coupling reactions including Heck-, Suzuki-, Sonohashira-Hagihara, carbonyl-hydrocyanation, -arylation and hydrosilylations, olefin hydrosilylation reactions as well as various metathesis-based reactions. Finally, suitable immobilization technologies allow for generating immobilized catalysts for continuous flow applications[7-12]

figure-1

References:
[1] S. Naumann, M. R. Buchmeiser, Catal. Sci. Technol., 4, 2014, 2466-2479.
[2] B. Bantu, G. M. Pawar, U. Decker, Klaus Wurst, A. M. Schmidt, M. R. Buchmeiser, Chem. Eur. J.,15,  2009, 3103-3109.
[3] S. Naumann, S. Epple, C. Bonten, M. R. Buchmeiser, ACS Macro Lett., 2, 2013, 609-612.
[4] S. Naumann, F. G. Schmidt, M. R. Buchmeiser, Polym. Chem., 4, 2013, 4172-4181.
[5] S. Naumann, F.-G. Schmidt, R. Schowner, W. Frey, M. R. Buchmeiser, Polym. Chem., 4, 2013, 2731-2740.
[6] S. Naumann, M. Speiser, R. Schowner, E. Giebel, M. R. Buchmeiser, Macromolecules, 47, 2014, 4548-4556.
[7] G. M. Pawar, M. R. Buchmeiser, Adv. Synth. Catal., 352(5), 2010, 917-928.
[8] G. Pawar, B., Bantu, J. Weckesser, S. Blechert, K. Wurst, M. R. Buchmeiser, Dalton Trans., 2009, 9043-9051.
[9] M. Lichtenheldt, D. Wang, K. Vehlow, I. Reinhardt, C. Kühnel, U. Decker, S. Blechert, M. R. Buchmeiser, Chem. Eur. J., 15, 2009, 9451-9457.
[10]P. S. Kumar, K. Wurst, M. R. Buchmeiser, Organometallics, 28, 2009, 1785-1790.
[11] M. R. Buchmeiser, Chem. Rev., 109(2), 2009, 303-321.
[12] K. Velow, D. Wang, S. Blechert, M. R. Buchmeiser, Angew. Chem., 120, 2008, 2655-2658; Angew. Chem. Int. Ed., 47, 2008, 2615-2618.