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Phenalenannulations: Three‐Point Double Annulation Reactions that Convert Benzenes into Pyrenes
Author(s) -
Kawade Rahul Kisan,
Hu Chaowei,
Dos Santos Nikolas R.,
Watson Noelle,
Lin Xinsong,
Hanson Kenneth,
Alabugin Igor V.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202006087
Subject(s) - annulation , chemistry , moiety , ring (chemistry) , pyrene , benzene , naphthalene , stereochemistry , organic chemistry , catalysis
3‐Point annulations, or phenalenannulations, transform a benzene ring directly into a substituted pyrene by “wrapping” two new cycles around the perimeter of the central ring at three consecutive carbon atoms. This efficient, modular, and general method for π‐extension opens access to non‐symmetric pyrenes and their expanded analogues. Potentially, this approach can convert any aromatic ring bearing a ‐CH 2 Br or a ‐CHO group into a pyrene moiety. Depending upon the workup choices, the process can be directed towards either tin‐ or iodo‐substituted product formation, giving complementary choices for further various cross‐coupling reactions. The two‐directional bis‐double annulation adds two new polyaromatic extensions with a total of six new aromatic rings at a central core.