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:

URL	URL Type	Description
http://dx.doi.org/10.1002/ejoc.201500276	DOI	Article
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500276/abstract	Publisher	Article
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500276/suppinfo	Publisher	Supporting Information

ORCID:

Author	ORCID
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 Agency	Grant Number
Doheny Eye Institute	UNSPECIFIED
Sanofi	UNSPECIFIED
Gordon and Betty Moore Foundation	UNSPECIFIED
Caltech	UNSPECIFIED
NIH	RR027690

Subject Keywords:

Synthetic methods; Oligomerization; Reaction mechanisms; Stereoisomerism; Corroles

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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

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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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