Premium
N‐Confused Phlorin‐Prodigiosin Chimera: meso ‐Aryl Oxidation and π‐Extension Triggered by Peripheral Coordination
Author(s) -
Su Guangxian,
Li Qizhao,
Ishida Masatoshi,
Li Chengjie,
Sha Feng,
Wu XinYan,
Wang Lu,
Baryshnikov Glib,
Li Dawei,
Ågren Hans,
Furuta Hiroyuki,
Xie Yongshu
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913290
Subject(s) - prodigiosin , chimera (genetics) , peripheral , aryl , chemistry , extension (predicate logic) , medicine , computer science , biochemistry , organic chemistry , escherichia coli , alkyl , serratia marcescens , gene , programming language
An N‐confused phlorin isomer bearing a dipyrrin moiety at the α‐position of the confused pyrrole ring ( 1 ) was synthesized. Pd II and B III coordination at the peripheral prodigiosin‐like moiety of 1 afforded the corresponding complexes 2 and 3 . Reflux of 2 in triethylamine (TEA) converted the meso ‐phenyl into the Pd II ‐coordinating phenoxy group to afford 4 . Under the same reaction conditions, TEA was linked to the α‐position of the dipyrrin unit in 3 as an N,N‐diethylaminovinyl group to afford 5 . Furthermore, peripheral coordination of B III in 3 and 5 improved the planarity of the phlorin macrocycle and thus facilitated the coordination of Ag III at the inner cavity to afford 3‐Ag and 5‐Ag , respectively. These results provide an effective approach for developing unique porphyrinoids through peripheral coordination.