Acyl Radical Smiles Rearrangement To Construct Hydroxybenzophenones by Photoredox Catalysis.

Org Lett

State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 China.

Published: April 2019

The first visible-light-induced acyl radical Smiles rearrangement to transform biaryl ethers to hydroxybenzophenones under mild and metal-free conditions is reported. Using the dual catalysis of hypervalent iodine(III) reagents and organophotocatalysts, ketoacids readily generate acyl radicals and undergo 1,5- ipso addition. This method can construct electron-deficient and electron-rich hydroxybenzophenones with excellent chemoselectivity and on gram scale. The performance of the reaction in neutral aqueous conditions holds potential for future biomolecule applications.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.9b00353DOI Listing

Publication Analysis

Top Keywords

acyl radical
8
radical smiles
8
smiles rearrangement
8
rearrangement construct
4
construct hydroxybenzophenones
4
hydroxybenzophenones photoredox
4
photoredox catalysis
4
catalysis visible-light-induced
4
visible-light-induced acyl
4
rearrangement transform
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!