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. 2021 Jul 21;11(41):25207-25210.
doi: 10.1039/d1ra04130d. eCollection 2021 Jul 19.

Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids

Alisha Rani Tripathy  1 , Girish Suresh Yedase  1 , Veera Reddy Yatham  1
Affiliations

Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids

Alisha Rani Tripathy et al. RSC Adv. .

Abstract

We report herein a cerium photocatalyzed aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement. This operationally simple protocol utilizes inexpensive CeCl3 as a photocatalyst and converted a variety of 2-aryloxybenzoic acids into aryl-2-hydroxybenzoates in good yields.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Known reports for 1,5-aryl migration of 2-aryloxybenzoic acids.
Scheme 1
Scheme 1. Cerium photocatalyzed 1,5-aryl migration of 2-aryloxybenzoic acids. Reaction conditions as given in Table 1 (entry 1). Isolated yields, average of at least two independent runs. a30 h reaction time. b80 h reaction time. c36 h reaction time.
Scheme 2
Scheme 2. Plausible mechanism for 1,5-aryl migration of 2-aryloxybenzoic acids.
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