Macrocyclic Transformations from Norrole to Isonorrole and an N-Confused Corrole with a Fused Hexacyclic Ring System Triggered by a Pyrrole Substituent.

Research output: Research - peer-reviewArticle

  • External authors:
  • Miao Li
  • Pingchun Wei
  • Masatoshi Ishida
  • Xin Li
  • Mathew Savage
  • Rui Guo
  • Zhongping Ou
  • Hiroyuki Furuta
  • Yongshu Xie


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-Cmeso -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-CAr -fused N-confused corroles, L3 and L4, respectively. L3 and L4 contain fused []-tetra- and []-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.

Bibliographical metadata

Original languageEnglish
Pages (from-to)3063-3067
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number9
Early online date28 Jan 2016
StatePublished - 24 Feb 2016