Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates

Pratheepkumar Annamalai, Huan Chang Hsiao, Selvam Raju, Yi Hsuan Fu, Pei Ling Chen, Jia Cherng Horng, Yi Hung Liu, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A palladium-catalyzed C-H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C-H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C-H bond functionalizations. Additionally, nondirected C-H bond functionalization at the C-4′ position with alkenes rendered complete C-H functionalization of five C-H bonds that formed a stable hexasubstituted benzene ring.

Original languageEnglish
Pages (from-to)1182-1186
Number of pages5
JournalOrganic Letters
Volume21
Issue number4
DOIs
StatePublished - 15 Feb 2019

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