Literature DB >> 25171579

Transition metal-free direct C-H functionalization of quinones and naphthoquinones with diaryliodonium salts: synthesis of aryl naphthoquinones as β-secretase inhibitors.

Dawei Wang1, Bingyang Ge, Liang Li, Jie Shan, Yuqiang Ding.   

Abstract

A novel ligand-free, transition metal-free direct C-H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.

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Year:  2014        PMID: 25171579     DOI: 10.1021/jo501467v

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  Late-Stage C-H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines.

Authors:  Álvaro Gutiérrez-Bonet; Camille Remeur; Jennifer K Matsui; Gary A Molander
Journal:  J Am Chem Soc       Date:  2017-08-23       Impact factor: 15.419

2.  A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.

Authors:  Linlin Qin; Bao Hu; Kiel D Neumann; Ethan J Linstad; Katelyenn McCauley; Jordan Veness; Jayson J Kempinger; Stephen G DiMagno
Journal:  European J Org Chem       Date:  2015-08-14

3.  Flow Synthesis of Diaryliodonium Triflates.

Authors:  Gabriele Laudadio; Hannes P L Gemoets; Volker Hessel; Timothy Noël
Journal:  J Org Chem       Date:  2017-07-20       Impact factor: 4.354

4.  Iron catalyzed C-C dehydrogenative coupling reaction: synthesis of arylquinones from quinones/hydroquinones.

Authors:  Yu Dong; Chun Xie; Jia Chen; Ai Shen; Qi-Qi Luo; Bing He; Zhi-Fan Wang; Bo Chang; Fan Yang; Zhi-Chuan Shi
Journal:  RSC Adv       Date:  2022-01-28       Impact factor: 3.361

5.  Photochemical C-H Arylation of Napthoquinones Using Eosin Y.

Authors:  Bhawana Nagar; Basab Bijayi Dhar
Journal:  ACS Omega       Date:  2022-08-31

6.  Regioselective Oxidative Arylation of Fluorophenols.

Authors:  Congjun Yu; Frederic W Patureau
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-31       Impact factor: 15.336

  6 in total

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