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Macrocyclic Transformations from Norrole to Isonorrole and an N‐Confused Corrole with a Fused Hexacyclic Ring System Triggered by a Pyrrole Substituent
Author(s) -
Li Miao,
Wei Pingchun,
Ishida Masatoshi,
Li Xin,
Savage Mathew,
Guo Rui,
Ou Zhongping,
Yang Sihai,
Furuta Hiroyuki,
Xie Yongshu
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510879
Subject(s) - corrole , pyrrole , ring (chemistry) , moiety , chemistry , substituent , stereochemistry , annulation , photochemistry , organic chemistry , catalysis
Three kinds of fused porphyrinoids, L2 – L4 , possessing different types of corrole‐based frameworks were synthesized from a pyrrole‐substituted corrole isomer (norrole L1 ). Oxidation of L1 afforded a unique N‐C meso ‐fused pyrrolyl isonorrole L2 , involving the fusion of an auxiliary pyrrolic NH moiety with a meso‐sp 3 ‐hybridized carbon atom. Subsequently, L2 underwent macrocycle transformations to give singly and doubly N‐C Ar ‐fused N‐confused corroles, L3 and L4 , respectively. L3 and L4 contain fused [5.7.6.5]‐tetra‐ and [5.6.7.7.6.5]‐hexacyclic structures, respectively, prepared through lateral annulation. These skeletal transformation reactions from norrole to its isomer isonorrole and finally to N‐confused corrole indicate that multiply fused porphyrinoids could be readily synthesized from pyrrole‐appended confused porphyrinoids.