Journal article

Authors list: Ochmann, L; Fuhrmann, M; Gössl, FJ; Makaveev, A; Schreiner, PR

Publication year: 2022

Pages: 6968-6972

Journal: Organic Letters

Volume number: 24

Issue number: 38

ISSN: 1523-7060

eISSN: 1523-7052

DOI Link: https://doi.org/10.1021/acs.orglett.2c02780

Publisher: American Chemical Society

Abstract: 
We report a general and scalable method for the synthesis of all-meta-trisubstituted benzenes from readily available 3,5-disubstituted catechols. Oxidation and [4 + 2] cycloaddition with acetylene dienophiles generate a bicyclo[2.2.2]octane structure that is doubly decarbonylated initiated by blue-light irradiation, leading to a meta,meta-disubstitution pattern on the re-aromatized system. This enables this substitution pattern even with very bulky alkyl groups (deemed excellent dispersion energy donors) to be incorporated into, for example, chiral phosphoric acid catalysts.

Harvard Citation style: Ochmann, L., Fuhrmann, M., Gössl, F., Makaveev, A. and Schreiner, P. (2022) All That metas-Synthesis of Dispersion Energy Donor-Substituted Benzenes, Organic Letters, 24(38), pp. 6968-6972. https://doi.org/10.1021/acs.orglett.2c02780

APA Citation style: Ochmann, L., Fuhrmann, M., Gössl, F., Makaveev, A., & Schreiner, P. (2022). All That metas-Synthesis of Dispersion Energy Donor-Substituted Benzenes. Organic Letters. 24(38), 6968-6972. https://doi.org/10.1021/acs.orglett.2c02780