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New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et3SiH/KOtBu

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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.

Graphical abstract: New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et3SiH/KOtBu

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Article information


Submitted
18 Jan 2020
Accepted
11 Mar 2020
First published
11 Mar 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et3SiH/KOtBu

A. J. Smith, D. Dimitrova, J. N. Arokianathar, K. Kolodziejczak, A. Young, M. Allison, D. L. Poole, S. G. Leach, J. A. Parkinson, T. Tuttle and J. A. Murphy, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC00361A

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