Issue 12, 2019

Functionalized spirolactones by photoinduced dearomatization of biaryl compounds

Abstract

The idea of using biaryl structures to generate synthetic building blocks such as spirolactones is attractive because biaryl structures are abundant in biomass waste streams. However, the inertness of aromatic rings of biaryls makes it challenging to transform them into functionalized structures. In this work, we developed photoinduced dearomatization of nonphenolic biaryl compounds to generate spirolactones. We demonstrate that dearomatization can be performed via either aerobic photocatalysis or anaerobic photooxidation to tolerate specific synthetic conditions. In both pathways, dearomatization is induced by electrophilic attack of the carboxyl radical. The resulting spirodiene radical is captured by either oxygen or water in aerobic and anaerobic systems, respectively, to generate the spirodienone. These methods represent novel routes to synthesize spirolactones from the biaryl motif.

Graphical abstract: Functionalized spirolactones by photoinduced dearomatization of biaryl compounds

Supplementary files

Article information

Article type
Edge Article
Submitted
07 Dec. 2018
Accepted
18 Febr. 2019
First published
19 Febr. 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 3681-3686

Functionalized spirolactones by photoinduced dearomatization of biaryl compounds

H. Li, E. Subbotina, A. Bunrit, F. Wang and J. S. M. Samec, Chem. Sci., 2019, 10, 3681 DOI: 10.1039/C8SC05476B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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