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

Miao Li, Pingchun Wei, Masatoshi Ishida, Xin Li, Mathew Savage, Rui Guo, Zhongping Ou, Sihai Yang, Hiroyuki Furuta, Yongshu Xie

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Abstract

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-sp3-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 [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.

Original languageEnglish
Pages (from-to)3063-3067
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number9
DOIs
Publication statusPublished - Feb 24 2016

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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