Designed synthesis of new ortho-carborane derivatives: from mono- to polysubstituted frameworks |
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Authors: | Barberà Gemma Vaca Albert Teixidor Francesc Sillanpää Reijo Kivekäs Raikko Viñas Clara |
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Institution: | Institut de Ciencia de Materials de Barcelona (CSIC) Campus UAB, 08193 Bellaterra, Spain. |
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Abstract: | The use of nucleophilic and electrophilic processes allow the designed synthesis of several B-iodinated derivatives of o-carborane. Because of the straightforward Pd-catalyzed conversion of B-I to B-C bond with Grignard reagents, such as methylMgBr and biPhenylMgBr, both, symmetrical 3,6-R 2-1,2- closo-C 2B 10H 10 and asymmetrical 3-I-6-Me-1,2- closo-C 2B 10H 10 could be obtained. Not only conventional reactions in solution have been studied but also a highly efficient, clean and fast solvent-free procedure has provided successful results to regioselectively produce B-iodinated o-carborane derivatives by a careful control of the reaction conditions. The high number of nonequivalent leaving groups in boron iodinated o-carborane derivatives opens the possibility through B-C coupling to materials with novel possibilities and to self-assembling due to the enhanced polarizability of the C-H bond. |
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