[22]Pentaphyrins(2.0.1.1.0) Displaying N‐Fusion, Pyrrole‐Rearrangement, and Dimerization Reactions Upon Oxidation and Metalation

Author:

Chen Jinchao1,Liu Le1,Rao Yutao1,Xu Ling1,Zhou Mingbo1,Yin Bangshao1,Shimizu Soji2,Shimizu Daiki3,Osuka Atsuhiro1,Song Jianxin1ORCID

Affiliation:

1. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Ministry of Educational of China Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province College of Chemistry and Chemical Engineering Hunan Normal University 410081 Changsha China

2. Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University 819-0395 Fukuoka Japan

3. Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University Nishikyo-ku 615-8510 Kyoto Japan

Abstract

AbstractExploration of expanded porphyrins with unprecedented reactivities has remained important. Here [22]pentaphyrins(2.0.1.1.0) were synthesized as a constitutional isomer of sapphyrin by acid‐catalyzed cyclization of 1,14‐dibromo‐5,10‐diaryltripyrrin with 1,2‐di(pyrro‐2‐ly)ethenes. These pentaphyrins display roughly planar structures and varying aromaticities depending upon the vinylene structures. The 19,20‐ditolyl pentaphyrin gave an N‐fused product and an unprecedented pyrrole‐rearranged product, depending upon the oxidation conditions. Remarkably, upon the metalation with CuCl, the N‐fused product and the pyrrole‐rearranged product afforded an inner ββ coupled face‐to‐face CuII complex dimer and an outer ββ coupled lateral CuII complex dimer, respectively, in fairly good yields. Further, [22]pentaphyrin(2.0.1.1.0) fused with a NiII porphyrin was effectively dimerized upon oxidation with MnO2 to give a 16–16’ directly linked dl‐dimer.

Funder

National Natural Science Foundation of China

Hunan Provincial Innovation Foundation for Postgraduate

Publisher

Wiley

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