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

doi:10.1021/acs.orglett.9b00119

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

Org Lett. 2019 Feb 15;21(4):1182-1186. doi: 10.1021/acs.orglett.9b00119. Epub 2019 Feb 4.

Authors

Pratheepkumar Annamalai¹, Huan-Chang Hsiao¹, Selvam Raju¹, Yi-Hsuan Fu², Pei-Ling Chen², Jia-Cherng Horng², Yi-Hung Liu³, Shih-Ching Chuang¹

Affiliations

¹ Department of Applied Chemistry , National Chiao Tung University , Hsinchu 30010 , Taiwan.
² Department of Chemistry , National Tsing Hua University , Hsinchu 30010 , Taiwan.
³ Instrumentation Center , National Taiwan University , Taipei 10617 , Taiwan.

PMID: 30714383
DOI: 10.1021/acs.orglett.9b00119

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.

Publication types

Research Support, Non-U.S. Gov't