One-Pot Approach to Chlorins, Isobacteriochlorins, Bacteriochlorins, and Pyrrocorphins

Morten K Peters; Fynn Röhricht; Christian Näther; Rainer Herges

doi:10.1021/acs.orglett.8b03433

One-Pot Approach to Chlorins, Isobacteriochlorins, Bacteriochlorins, and Pyrrocorphins

Org Lett. 2018 Dec 21;20(24):7879-7883. doi: 10.1021/acs.orglett.8b03433. Epub 2018 Dec 11.

Authors

Morten K Peters¹, Fynn Röhricht¹, Christian Näther², Rainer Herges¹

Affiliations

¹ Otto Diels-Institute of Organic Chemistry , Christian Albrechts University Kiel , Otto Hahn Platz 4 , 24118 Kiel , Germany.
² Institut für Anorganische Chemie , Christian Albrechts University Kiel , Max-Eyth-Strasse 2 , 24118 Kiel , Germany.

PMID: 30525702
DOI: 10.1021/acs.orglett.8b03433

Abstract

A Diels-Alder strategy is reported to synthesize the complete set of hydroporphyrins: chlorins, bacteriochlorins, isobacteriochlorins, and pyrrocorphins. Porphyrins and Ni-porphyrins react with isobenzofuran in very high yields at 70 °C to form the corresponding chlorins. Electron-deficient porphyrins react with a second equivalent of isobenzofuran yielding exclusively bacteriochlorin (82%), and Ni-porphyrin gives only isobacteriochlorin (99%). All cycloadditions are completely regio- and stereoselective. The regiochemistry is correctly predicted using the ACID method.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Models, Molecular
Molecular Structure
Porphyrins / chemical synthesis*
Porphyrins / chemistry
Stereoisomerism

Substances

Porphyrins
bacteriochlorin
isobacteriochlorin
chlorin