New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et3SiH/KOtBu. Issue 14 (20th March 2020)

• Record Type: Journal Article
• Authors: Smith, Andrew J.; Dimitrova, Daniela; Arokianathar, Jude N.; Kolodziejczak, Krystian; Young, Allan; Allison, Mark; Poole, Darren L.; Leach, Stuart G.; Parkinson, John A.; Tuttle, Tell; Murphy, John A.
• Is Part Of: Chemical science. Volume 11:Issue 14(2020)
• Page Start: 3719
• Page End: 3726
• Publication Date: 2020-03-20
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc00361a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : N -Arylindoles are transformed into dihydroacridines in a new type of rearrangement, through heating with triethylsilane and potassium tert- butoxide. Abstract : N -Arylindoles are transformed into dihydroacridines in a new type of rearrangement, through heating with triethylsilane and potassium tert- butoxide. Studies indicate that the pathway involves (i) the formation of indole radical anions followed by fragmentation of the indole C2–N bond, and (ii) a ring-closing reaction that follows a potassium-ion dependent hydrogen atom transfer step. Unexpected behaviors of 'radical-trap' substrates prove very helpful in framing the proposed mechanism.