Design and synthesis of 3,3'-triazolyl biisoquinoline N , N' -dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles.

A new strategy to effectively lock the conformation of substituents at the 3,3'-positions of axial-chiral biisoquinoline N , N' -dioxides was developed based on the strong dipole-dipole interaction between 1,2,3-triazole and pyridine N -oxide rings. The crystal structure and the DFT calculations of 3,3'-bis(1-benzyl-1 H -1,2,3-triazole-4-yl)-1,1'-biisoquinoline N , N' -dioxide ( 3a ) provided strong support for this strategy. Furthermore, we successfully demonstrated that readily available 4-trimethylsilyl-1,2,3-triazoles are viable nucleophiles for Hiyama cross-coupling.
Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.