Radical–anion coupling through reagent design: hydroxylation of aryl halides. Issue 43 (28th October 2021)

• Record Type: Journal Article
• Authors: Greener, Andrew J.; Ubysz, Patrycja; Owens-Ward, Will; Smith, George; Ocaña, Ivan; Whitwood, Adrian C.; Chechik, Victor; James, Michael J.
• Is Part Of: Chemical science. Volume 12:Issue 43(2021)
• Page Start: 14641
• Page End: 14646
• Publication Date: 2021-10-28
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc04748e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described. Abstract : The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described. Key to the success of this approach was the identification of a reducing oxime anion which can interact and couple with open-shell aryl radicals. Experimental and computational studies support the proposed radical-nucleophilic substitution chain mechanism.