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

TETRAHEDRON LETTERS

卷:81

Article

Sun, Shiyu¹  Reep, Carlyn¹  Zhang, Chenrui¹  Captain, Burjor²  Peverati, Roberto¹  Takenaka, Norito¹ 

[1] Florida Inst Technol, Dept Biomed & Chem Engn & Sci, Chem Program, 150 West Univ Blvd, Melbourne, FL 32901 USA

[2] Univ Miami, Dept Chem, 1301 Mem Dr, Coral Gables, FL 33146 USA

关键词: axial-chiral Lewis bases;    1,2,3-triazoles;    Hiyama cross-coupling;    Catalyst design;    Computational chemistry;   

DOI  :  10.1016/j.tetlet.2021.153338

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

Free