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Control of Oligomerization and Oxidation Steps in the Synthesis of Tris(pentafluorophenyl)corrole
Author(s) -
Blumenfeld Carl,
Fisher Katherine J.,
Henling Lawrence M.,
Grubbs Robert H.,
Gray Harry B.,
Virgil Scott C.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500276
Subject(s) - corrole , chemistry , yield (engineering) , tris , pyrrole , mass spectrometry , combinatorial chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , photochemistry , chromatography , biochemistry , materials science , metallurgy
The mechanistic features of oligomerization and oxidative cyclization steps in the synthesis of tris(pentafluorophenyl)corrole ( 1 ) have been thoroughly studied. Separation of the intermediates by preparative HPLC and analysis by NMR spectroscopy and high resolution mass spectrometry allowed for the identification of product‐forming intermediates and monitoring of undesired byproducts. Conditions for complete end‐capping with pyrrole were optimized for improved yields of oligomers leading to the desired corrole 1 . A yield of 84 % was achieved during oxidation of an isolated precursor; the overall yield of 1 was 17.0 %.