Synthesis of Symmetric Diaryl Secondary Amine Ligands via C-N Cross-Coupling and Subsequent Synthesis of Monomeric Aluminum Complexes
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Abstract Two novel variants of N,N ’ -Diphenyl-1,2-benzenediamine were synthesized via Buchwald-Hartwig C-N Cross-Coupling and a subsequent complexation of the purified ligand with aluminum was then attempted. The synthesis of diamine employed Pd(OAc) 2 with t Bu 3 P ligand to form a transition metal catalyst system using NaO t Bu for basic elimination. Both microwave and thermal heating methods were attempted. Thermal reactions to give 1,2-bis(mesitylamino)tetramethylbenzene ( 1 ) (44% yield) and 1,2-bis(m-xylylamino)tetramethylbenzene ( 2 ) (90% yield) were high yield and purified product was verified by NMR when . A purification using cold hexanes was performed giving near 100% product purity. Purification using cold methanol was also attempted but yielded significantly less product of both 1 (14% reduced yield) and 2 (49% reduced yield). Formation of the target complexes 1,2-bis(mesitylamino)tetramethylbenzenemethylaluminum ( 3 ) and 1,2-bis( m-xylylamino )tetramethylbenzenemethylaluminum ( 4 ) via reaction of ( 1 ) and ( 2 )n with trimethylaluminum was attempted. Synthesis of 3 and 4 did not succeed in initial reactions and further study and modifications of procedures is recommended.