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Triphenylsilane‐fused Porphyrins
Author(s) -
Kato Kenichi,
Kim Jun Oh,
Yorimitsu Hideki,
Kim Dongho,
Osuka Atsuhiro
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600424
Subject(s) - negishi coupling , porphyrin , intramolecular force , chemistry , sequence (biology) , atom (system on chip) , crystallography , stereochemistry , photochemistry , medicinal chemistry , catalysis , organic chemistry , biochemistry , computer science , embedded system
A reaction sequence of 2‐(diphenylsilyl)phenylation by Negishi coupling and intramolecular sila‐Friedel–Crafts reaction has been explored for the synthesis of mono‐triphenylsilane‐fused porphyrins 5 M and 6 M (M= Ni, Zn) and bis‐triphenylsilane‐fused porphyrins 7 M and 8 Ni . A triply linked triphenylsilane‐fused Ni II porphyrin, 13 Ni , was synthesized in a stepwise manner involving the above reaction sequence and a final Pd‐catalyzed C−H activating arylative cyclization. The silicon atom in 13 Ni takes a distorted planarized structure with an almost perpendicular Si‐phenyl group, causing an electronic effect due to effective σ*–π* interaction.