title: Synthesis of tri-substituted biaryl based trianglimines: formation of C3-symmetrical and non-symmetrical regioisomers.
abstract: 2-Functionalised aromatic monoaldehydes were synthesised in good to excellent yields by reacting 4-bromo-2-fluorobenzaldehyde with different secondary amines and phenol. The Suzuki-coupling reaction of the newly functionalised aromatic monoaldehydes with 4-formylphenylboronic acid afforded the corresponding 2-functionalised-4,4'-biphenyldialdehydes in good yields (47-85%). The [3+3]-cyclocondensation reactions of the 2-functionalised-4,4'-biphenyldialdehydes with (1R,2R)-1,2-diaminocyclohexane afforded a mixture of regioisomeric C(3)-symmetrical and non-symmetrical trianglimines. Reduction of the C(3)-symmetrical and the non-symmetrical trianglimines with NaBH(4) in a mixture of THF and MeOH afforded the corresponding trianglamines in high yields.
authors: School of Engineering and Science, Jacobs University Bremen, P.O. Box 750 561, 28725 Bremen, Germany.
authors: Hany F
authors: HF
authors: Nour
authors: Marius F
authors: MF
authors: Matei
authors: Bassem S
authors: BS
authors: Bassil
authors: Ulrich
authors: U
authors: Kortz
authors: Nikolai
authors: N
authors: Kuhnert