Pentiptycene building blocks derived from nucleophilic aromatic substitution of pentiptycene triflates and halides

Sandip Kumar Kundu; Wei Shyang Tan; Jyu-Lun Yan; Jye-Shane Yang

doi:10.1021/jo100812z

Pentiptycene building blocks derived from nucleophilic aromatic substitution of pentiptycene triflates and halides

J Org Chem. 2010 Jul 2;75(13):4640-3. doi: 10.1021/jo100812z.

Authors

Sandip Kumar Kundu¹, Wei Shyang Tan, Jyu-Lun Yan, Jye-Shane Yang

Affiliation

¹ Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617.

PMID: 20533833
DOI: 10.1021/jo100812z

Abstract

The nucleophilic aromatic substitution (S(N)Ar) reactions of the nitro-substituted pentiptycene triflate 15 with LiBr and LiI and the resulting halides 18 and 19 with N(3)(-), CN(-), and ArS(-) in DMF provide an efficient route toward pentiptycene halides and dihalides and other new pentiptycene building blocks. The reactivity of diaminopentiptycene in Pd-catalyzed C-N coupling reactions is also demonstrated.