Issue 14, 2020

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2020,11, 3719-3726

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, 11, 3719 DOI: 10.1039/D0SC00361A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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