Premium
Regioselective Nucleophilic Functionalization of Antiaromatic Nickel(II) Norcorroles
Author(s) -
Nozawa Ryo,
Yamamoto Keitaro,
Shin JiYoung,
Hiroto Satoru,
Shinokubo Hiroshi
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502666
Subject(s) - antiaromaticity , regioselectivity , thiophenol , chemistry , nickel , cyanide , nucleophile , nucleophilic substitution , catalysis , photochemistry , aromaticity , organic chemistry , molecule
Treatment of antiaromatic nickel(II) norcorrole with potassium cyanide provided nickel(II) 3‐cyanonorcorrole with perfect regioselectivity without the help of a catalyst. The reaction of the nickel(II) norcorrole with phenol or thiophenol in the presence of a base also yielded substitution products. The antiaromatic 16π conjugation system in the norcorrole core was preserved in the functionalized products. Introduction of phenylthio groups significantly decreased the HOMO–LUMO gap and enhanced the near IR absorption property.