Control of Oligomerization and Oxidation Steps in the Synthesis of Tris(pentafluorophenyl)corrole

Abstract

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 %.

Additional Information

© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Received: February 27, 2015. Article first published online: 1 Apr. 2015. The authors acknowledge the Doheny Eye Institute, Sanofi, the Gordon and Betty Moore Foundation, Caltech, and the National Institutes of Health (NIH) (grant number RR027690) for financial and infrastructural support. The authors are grateful to Professor Zeev Gross for ongoing support in these efforts and suggestions on the presentation of this work. The authors also wish to thank Dr. David VanderVelde for assistance in obtaining NMR spectra of compounds 4-10 and Prof. Brian Stoltz for helpful discussions.

Attached Files

Supplemental Material - ejoc_201500276_sm_miscellaneous_information.pdf

Files

Additional details