Premium
Synthesis of Indolophanes by Photochemical Macrocyclization
Author(s) -
Pfaffenbach Magnus,
Roller Alexander,
Gaich Tanja
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600835
Subject(s) - atropisomer , regioselectivity , chemistry , ring (chemistry) , photochemistry , closure (psychology) , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , economics , market economy
Herein, we report the synthetically practical, short, and general access to novel indolophane architectures by means of a photochemical C−H activation process—the Witkop cyclization. These highly strained scaffolds were obtained by photoinduced ring closure and feature atropisomerism as well as aromatic ring current effects, which both have been investigated. The prevailing regioselectivity of theWitkop cyclization reaction was completely reversed by the presence of a quaternary carbon center, exerting a strong Thorpe–Ingold effect on the system for which experimental‐evidence is provided.