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

Blumenfeld, Carl and Fisher, Katherine J. and Henling, Lawrence M. and Grubbs, Robert H. and Gray, Harry B. and Virgil, Scott C. (2015) Control of Oligomerization and Oxidation Steps in the Synthesis of Tris(pentafluorophenyl)corrole. European Journal of Organic Chemistry, 2015 (14). pp. 3022-3025. ISSN 1434-193X. https://resolver.caltech.edu/CaltechAUTHORS:20150406-084337401

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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 %.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/ejoc.201500276DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500276/abstractPublisherArticle
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500276/suppinfoPublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Gray, Harry B.0000-0002-7937-7876
Virgil, Scott C.0000-0001-8586-5641
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.
Funders:
Funding AgencyGrant Number
Doheny Eye InstituteUNSPECIFIED
SanofiUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
NIHRR027690
Subject Keywords:Synthetic methods; Oligo­merization; Reaction mechanisms; Stereoisomerism; Corroles
Issue or Number:14
Record Number:CaltechAUTHORS:20150406-084337401
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150406-084337401
Official Citation:Blumenfeld, C., Fisher, K. J., Henling, L. M., Grubbs, R. H., Gray, H. B. and Virgil, S. C. (2015), Control of Oligomerization and Oxidation Steps in the Synthesis of Tris(pentafluorophenyl)corrole. Eur. J. Org. Chem., 2015: 3022–3025. doi: 10.1002/ejoc.201500276
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:56367
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:06 Apr 2015 20:09
Last Modified:09 Mar 2020 13:19

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