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

doi:10.1002/anie.201510879

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

Angew Chem Int Ed Engl. 2016 Feb 24;55(9):3063-7. doi: 10.1002/anie.201510879. Epub 2016 Jan 28.

Authors

Miao Li¹, Pingchun Wei¹, Masatoshi Ishida², Xin Li¹, Mathew Savage³, Rui Guo⁴, Zhongping Ou⁴, Sihai Yang³, Hiroyuki Furuta⁵, Yongshu Xie⁶

Affiliations

¹ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, 200237, P.R. China.
² Education Center for Global Leaders in Molecular Systems for Devices and Center for Molecular Systems, Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan.
³ School of Chemistry, University of Manchester, Manchester, m139pl, UK.
⁴ School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P.R. China.
⁵ Education Center for Global Leaders in Molecular Systems for Devices and Center for Molecular Systems, Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan. hfuruta@cstf.kyushu-u.ac.jp.
⁶ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, 200237, P.R. China. yshxie@ecust.edu.cn.

PMID: 26822959
DOI: 10.1002/anie.201510879

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-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 [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.

Keywords: N-confused corroles; aromaticity; corroles; fused-ring systems; porphyrinoids.

Publication types

Research Support, Non-U.S. Gov't