Discovery and Mechanistic Study of a Totally Organic C(aryl)-C(alkyl)Oxygen Insertion Reaction

Muhammad Kazim; Hayden Foy; Maxime A Siegler; Travis Dudding; Thomas Lectka

doi:10.1021/acs.joc.9b02238

Discovery and Mechanistic Study of a Totally Organic C_(aryl)-C_(alkyl)Oxygen Insertion Reaction

J Org Chem. 2019 Nov 1;84(21):14349-14353. doi: 10.1021/acs.joc.9b02238. Epub 2019 Oct 14.

Authors

Muhammad Kazim¹, Hayden Foy², Maxime A Siegler¹, Travis Dudding², Thomas Lectka¹

Affiliations

¹ Department of Chemistry , Johns Hopkins University , 3400 North Charles Street , Baltimore , Maryland 21218 , United States.
² Department of Chemistry , Brock University , 1812 Sir Isaac Brock Way , St. Catharines , ON L2S 3A1 , Canada.

PMID: 31577426
DOI: 10.1021/acs.joc.9b02238

Abstract

We report an unprecedented photochemical oxygen insertion reaction into an aromatic quinone methide. Insertion happens specifically within a C_(aryl)-C_(alkyl) bond, whereas the quinone methide moiety remains intact itself. Detailed mechanistic studies, supported by DFT calculations, support a pathway in which the p-QM plays a pivotal activating role.

Publication types

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