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

Several different projects entail the use of tailored N-heterocyclic carbenes (NHCs), e.g., 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. The thus prepared systems then serve as latent catalysts, e.g., for the synthesis of poly(urethane)s via reaction injection molding of one-component systems. 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.

References:
1) Polymer-Supported, Carbon Dioxide-Protected N-Heterocyclic Carbenes: Synthesis and Application in Organo- and Organometallic Catalysis, G. M. Pawar, M. R. Buchmeiser, Adv. Synth. Catal., 352 (5) 917-928 (2010)
2) Ring-Opening Metathesis Polymerization-Derived, Polymer-Bound Cu-Catalysts for Click-Chemistry and Hydrosilylation Reactions Under Micellar Conditions, G. Pawar, B., Bantu, J. Weckesser, S. Blechert, K. Wurst, M. R. Buchmeiser, Dalton Trans., 9043-9051 (2009)
3) Alternating Ring-Opening Metathesis Copolymerization by Grubbs-Type Initiators Based On Unsymmetrical N-Heterocyclic Carbenes, M. Lichtenheldt, D. Wang, K. Vehlow, I. Reinhardt, C. Kühnel, U. Decker, S. Blechert, M. R. Buchmeiser, Chem. Eur. J., 15, 9451-9457 (2009)
4) Ru-Alkylidene Metathesis Catalysts Based on 1,3-Dimesityl-4,5,6,7-tetrahydro-1,3-diazepin-2-ylidenes: Synthesis, Structure, and Activity, P. S. Kumar, K. Wurst, M. R. Buchmeiser, Organometallics, 28, 1785-1790 (2009)
5) Polymer-Supported Well-Defined Metathesis Catalysts, M. R. Buchmeiser, Chem. Rev., 109 (2), 303-321 (2009)
6) CO2- and SnII-Adducts of N-Heterocyclic Carbenes as Delayed Action Catalysts For Polyurethane Synthesis, B. Bantu, G. M. Pawar, U. Decker, Klaus Wurst, A. M. Schmidt, M. R. Buchmeiser, Chem. Eur. J., 15, 3103-3109 (2009)
7) Alternating Copolymerizations Using a Grubbs-Type Initiator Based on an Unsymmetrical, Chiral N-Heterocyclic Carbene, K. Velow, D. Wang, S. Blechert, M. R. Buchmeiser, Angew. Chem., 120, 2655-2658 (2008); Angew. Chem. Int. Ed., 47, 2615-2618 (2008)