Literature DB >> 30888188

Acyl Radical Smiles Rearrangement To Construct Hydroxybenzophenones by Photoredox Catalysis.

Junzhao Li1, Zhengyi Liu1, Shuang Wu1,2, Yiyun Chen1,2.   

Abstract

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.

Entities:  

Year:  2019        PMID: 30888188     DOI: 10.1021/acs.orglett.9b00353

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

Review 1.  Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

Authors:  Anthony R Allen; Efrey A Noten; Corey R J Stephenson
Journal:  Chem Rev       Date:  2021-10-21       Impact factor: 72.087

2.  Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.

Authors:  Satavisha Sarkar; Arghya Banerjee; Wang Yao; Eric V Patterson; Ming-Yu Ngai
Journal:  ACS Catal       Date:  2019-10-17       Impact factor: 13.084

Review 3.  Recent Synthetic Applications of the Hypervalent Iodine(III) Reagents in Visible-Light-Induced Photoredox Catalysis.

Authors:  Chaoyue Chen; Xin Wang; Tinghai Yang
Journal:  Front Chem       Date:  2020-09-23       Impact factor: 5.221

4.  Density Functional Theory Evaluation of a Photoinduced Intramolecular Aryl Ether Rearrangement.

Authors:  Péter Pál Fehér
Journal:  J Org Chem       Date:  2021-01-07       Impact factor: 4.354

5.  Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions.

Authors:  Hideyasu China; Nami Kageyama; Hotaka Yatabe; Naoko Takenaga; Toshifumi Dohi
Journal:  Molecules       Date:  2021-03-27       Impact factor: 4.411

  5 in total

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