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-ben-zyl-1H-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. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A new strategy was developed to effectively lock the conformation of substituents at the 3,3'-positions of axial-chiral biisoquinoline N,N'-dioxides based on the strong dipole-dipole interaction between 1,2,3-triazole and pyridine N-oxide rings. The crystal structure and DFT calculations of 3,3'-bis(1-ben-zyl-1H-1,2,3-triazole-4-yl)-1,1'-biisoquinoline N,N'-dioxide provided strong support for this strategy, and readily available 4-trimethylsilyl-1,2,3-triazoles were shown to be viable nucleophiles for Hiyama cross-coupling.