Synthesis of pyrrolidine-fused [34]- and [36]octaphyrins via 1,3-dipolar cycloaddition

Organic Letters
Hiroshi HataAtsuhiro Osuka

Abstract

[reaction: see text] The utility of expanded porphyrins as a dipolarophile in cycloaddition reactions has been investigated. The 1,3-dipolar cycloaddition of meso-octakis(pentafluorophenyl)[36]octaphyrin(1.1.1.1.1.1.1.1) with an azomethine ylide provides mono- and bis-pyrrolidine-fused octaphyrins regio- and stereoselectively. Treatment of the cycloadduct with MnO(2) afforded [34]octaphyrin quantitatively.

References

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Feb 19, 2002·Chemical Reviews·Ayub Jasat, David Dolphin
Sep 26, 2002·Chemical Communications : Chem Comm·Hiroyuki FurutaAtsuhiro Osuka
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Citations

Aug 9, 2016·Chemical Reviews·Masahiko Taniguchi, Jonathan S Lindsey
Aug 19, 2016·Chemical Reviews·Takayuki Tanaka, Atsuhiro Osuka
Aug 18, 2016·Chemistry : a European Journal·Flávio FigueiraJoão P C Tomé
Apr 30, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Yasuhide Inokuma, Atsuhiro Osuka
Aug 15, 2019·Chemistry : a European Journal·Sangya ChitranshiA Srinivasan
Mar 23, 2017·Frontiers in Chemistry·Nasarul Islam, Irfan H Lone
Apr 16, 2011·Angewandte Chemie·Marcin StępieńLechosław Latos-Grażyński
Jun 11, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ana F R CerqueiraAugusto C Tomé
Mar 22, 2019·Journal of the American Chemical Society·Bartosz SzyszkoLechosław Latos-Grażyński
Jul 29, 2006·The Journal of Organic Chemistry·Michał Gałezowski, Daniel T Gryko
Oct 26, 2006·Journal of the American Chemical Society·Zin Seok YoonDongho Kim

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