Azolium/Hydroquinone Organo‐Radical Co‐Catalysis: Aerobic C−C‐Bond Cleavage in Ketones. Issue 8 (18th January 2021)

• Record Type: Journal Article
• Authors: Nakatsuji, Yuya; Kobayashi, Yusuke; Masuda, Sakyo; Takemoto, Yoshiji
• Is Part Of: Chemistry. Volume 27:Issue 8(2021)
• Page Start: 2633
• Page End: 2637
• Publication Date: 2021-01-18
• Subjects: azolium salt -- EDA complex -- organocatalysis -- radical catalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202004943
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Organo‐radical catalysts have recently attracted great interest, and the development of this field can be expected to broaden the applications of organocatalysis. Herein, the first example of a radical‐generating system is reported that does not require any photoirradiation, radical initiators, or preactivated substrates. The oxidative C−C‐bond cleavage of 2‐substituted cyclohexanones was achieved using an azolium salt and a hydroquinone as co‐catalysts. A catalytic mechanism was proposed based on the results of diffusion‐ordered spectroscopy and cyclic voltammetry measurements, as well as computational studies. Abstract : Combine and conquer : A new method for the generation of radical species that does not require photoirradiation, radical initiators, or preactivated substrates is reported. The combined use of an azolium salt and hydroquinone generated an efficient catalytic system for the aerobic C−C‐bond cleavage of 2‐substituted ketones. A reaction mechanism is proposed based on the results of diffusion‐ordered spectroscopy and cyclic voltammetry measurements, as well as computational studies.