Efficient synthesis of benzo[c]cinnolines and azoarenes via dual C-N coupling of phthalhydrazide and trivalent halogen reagents

作者：Yang, Yanyan; Xie, Rongrong; Wang, Yiwen; Zhu, Peiyan; Wang, Jinhua; Li, Shiqing^*

来源：Organic Chemistry Frontiers, 2023, 10(11): 2701-2707.

DOI：10.1039/d3qo00391d

• PRIMARY AROMATIC-AMINES
• AZO-COMPOUNDS
• MERCURY(II) OXIDE
• BOND FORMATION
• H ACTIVATION
• ANILINES
• AZOBENZENES
• REDUCTION
• NANOPARTICLES
• DERIVATIVES

Phthalhydrazide has been proven to be an elegant N=N source to undergo tandem dual-C-N coupling/ deprotection/oxidation with not only cyclic/linear diaryliodoniums but also rarely explored diarylbromoniums, giving benzo[c]cinnolines (up to 99% yields) and azoarenes (mostly >90% yields) with broad scope. 3,3',4,4'-Tetraphenyl-1,1'-biisoquinoline serves as a privileged ligand for Cu-catalyzed C-N coupling for the first time. This method features base-mediated auto-deprotection of phthaloyl after Cu-catalyzed N,N'-diarylation in one pot, without extra steps for deprotection.

• 单位
  桂林理工大学