Regioselective phenylene-fusion reactions of Ni(ii)-porphyrins controlled by an electron-withdrawing meso -substituent

Chemical Science
Norihito FukuiAtsuhiro Osuka

Abstract

Oxidation of 10,15,20-triaryl Ni(ii)-porphyrins bearing an electron-withdrawing substituent at the 5-position with DDQ and FeCl3 gave 10,12- and 18,20-doubly phenylene-fused Ni(ii)-porphyrins regioselectively. A doubly phenylene-fused meso-chloro porphyrin thus prepared was reductively coupled to give a meso-meso linked dimer, which was further converted to a quadruply phenylene-fused meso-meso, β-β, β-β triply linked Zn(ii)-diporphyrin via inner-metal exchange followed by oxidation with DDQ and Sc(OTf)3. As compared to the usual meso-meso, β-β, β-β triply linked Zn(ii)-diporphyrin, this π-extended porphyrin dyad exhibits a smaller HOMO-LUMO gap and a larger two-photon absorption cross-section.

References

Dec 6, 2002·Journal of the American Chemical Society·Hyun Sun ChoAtsuhiro Osuka
May 22, 2004·Chemical Communications : Chem Comm·Simon Fox, Ross W Boyle
Oct 13, 2005·Chemical Reviews·Zhongfang ChenPaul von Ragué Schleyer
Jul 29, 2006·The Journal of Organic Chemistry·Michał Gałezowski, Daniel T Gryko
Nov 22, 2007·Journal of the American Chemical Society·Jaclyn M MurphyJohn F Hartwig
Feb 27, 2010·Organic Letters·Hong Wu, John Hynes
Apr 8, 2010·Organic Letters·Nicola K S DavisHarry L Anderson
Jul 6, 2010·Angewandte Chemie·Vyacheslav V DievMark E Thompson
May 24, 2011·The Journal of Organic Chemistry·Timothy D LashBradley A Godfrey
Jun 1, 2012·Chemical Communications : Chem Comm·Jan P Lewtak, Daniel T Gryko
Sep 20, 2012·Journal of the American Chemical Society·Yusuke MitsushigeYutaka Matsuo
May 30, 2013·Chemical Communications : Chem Comm·Tomoya IshizukaTakahiko Kojima
Jul 16, 2013·Angewandte Chemie·Marek GrzybowskiDaniel T Gryko
Aug 6, 2013·Angewandte Chemie·Norihito FukuiAtsuhiro Osuka
Aug 10, 2013·Chemical Communications : Chem Comm·Agnieszka Nowak-KrólDaniel T Gryko
Nov 28, 2013·Chemistry : a European Journal·Masaaki KitanoAtsuhiro Osuka
Jan 30, 2014·Organic Letters·Keisuke FujimotoAtsuhiro Osuka
Feb 1, 2014·Chemical Society Reviews·Takayuki Tanaka, Atsuhiro Osuka
May 14, 2014·Organic Letters·Kensuke OtaAtsuhiro Osuka
Jun 28, 2014·Chemical Communications : Chem Comm·Yuanyuan FangDaniel T Gryko
Jul 17, 2015·Chemistry : a European Journal·Keisuke FujimotoAtsuhiro Osuka
Jul 3, 1996·Journal of the American Chemical Society·Paul von Ragué SchleyerNicolaas J R van Eikema Hommes

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Citations

Jun 27, 2018·Chemistry : a European Journal·Takayuki Tanaka, Atsuhiro Osuka
Apr 28, 2020·Chemistry : a European Journal·Tomohiro HigashinoHiroshi Imahori
Jul 30, 2020·Angewandte Chemie·Hong WangFrancis D'Souza
Apr 30, 2017·Chemical Science·Norihito FukuiAtsuhiro Osuka
Jul 10, 2018·Angewandte Chemie·Qiang ChenAkimitsu Narita
Aug 21, 2019·Chemistry : a European Journal·Max M MartinNorbert Jux
May 5, 2018·Chemical Communications : Chem Comm·Mathieu BerthelotCharles H Devillers
Oct 7, 2016·Chemical Communications : Chem Comm·Maciej KrzeszewskiDaniel T Gryko
Jun 26, 2021·Chemical Science·Kazuya MiyagawaHiroshi Shinokubo
Jun 22, 2018·Journal of the American Chemical Society·Tomohiro NagaiHiroshi Shinokubo
Oct 12, 2021·Organic & Biomolecular Chemistry·Grigory L KozhemyakinIlya A Zamilatskov

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Methods Mentioned

BETA
X-ray

Software Mentioned

Gaussian
Gaussian 09

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