New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et(3)SiH/KO(t)Bu

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 rin...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152433/
https://www.ncbi.nlm.nih.gov/pubmed/34094060
http://dx.doi.org/10.1039/d0sc00361a
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author 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.
author_facet 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.
author_sort Smith, Andrew J.
collection PubMed
description 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.
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spelling pubmed-81524332021-06-03 New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et(3)SiH/KO(t)Bu 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. Chem Sci Chemistry 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. The Royal Society of Chemistry 2020-03-11 /pmc/articles/PMC8152433/ /pubmed/34094060 http://dx.doi.org/10.1039/d0sc00361a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
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.
New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et(3)SiH/KO(t)Bu
title New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et(3)SiH/KO(t)Bu
title_full New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et(3)SiH/KO(t)Bu
title_fullStr New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et(3)SiH/KO(t)Bu
title_full_unstemmed New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et(3)SiH/KO(t)Bu
title_short New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et(3)SiH/KO(t)Bu
title_sort new reductive rearrangement of n-arylindoles triggered by the grubbs–stoltz reagent et(3)sih/ko(t)bu
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152433/
https://www.ncbi.nlm.nih.gov/pubmed/34094060
http://dx.doi.org/10.1039/d0sc00361a
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