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

Andrew J. Smith; Daniela Dimitrova; Jude N. Arokianathar; Krystian Kolodziejczak; Allan Young; Mark Allison; Darren L. Poole; Stuart G. Leach; John A. Parkinson; Tell Tuttle; John A. Murphy

doi:10.1039/D0SC00361A

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

Andrew J. Smith, Daniela Dimitrova, Jude N. Arokianathar, Krystian Kolodziejczak, Allan Young, Mark Allison, Darren L. Poole, Stuart G. Leach, John A. Parkinson, Tell Tuttle, John A. Murphy

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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

Original language	English
Pages (from-to)	3719-3726
Number of pages	8
Journal	Chemical Science
Volume	11
Issue number	14
Early online date	11 Mar 2020
DOIs	https://doi.org/10.1039/D0SC00361A
Publication status	Published - 14 Apr 2020

Keywords

N-Arylindoles
Grubbs-Stoltz reagent
dihydroacridines

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Parkinson-etal-CS-2020-New-reductive-rearrangement-of-N-Arylindoles-triggered-by-the-Grubbs-Stoltz-reagentFinal published version, 1.25 MBLicence: CC BY 3.0

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@article{3e32061baf2941b2b13e9ac353a46cf9,

title = "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 {\textquoteleft}radical-trap{\textquoteright} substrates prove very helpful in framing the proposed mechanism",

keywords = "N-Arylindoles, Grubbs-Stoltz reagent, dihydroacridines",

author = "Smith, \{Andrew J.\} and Daniela Dimitrova and Arokianathar, \{Jude N.\} and Krystian Kolodziejczak and Allan Young and Mark Allison and Poole, \{Darren L.\} and Leach, \{Stuart G.\} and Parkinson, \{John A.\} and Tell Tuttle and Murphy, \{John A.\}",

year = "2020",

month = apr,

day = "14",

doi = "10.1039/D0SC00361A",

language = "English",

volume = "11",

pages = "3719--3726",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "14",

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TY - JOUR

T1 - New reductive rearrangement of N-Arylindoles triggered by the Grubbs-Stoltz reagent Et3SiH/KOtBu

AU - Smith, Andrew J.

AU - Dimitrova, Daniela

AU - Arokianathar, Jude N.

AU - Kolodziejczak, Krystian

AU - Young, Allan

AU - Allison, Mark

AU - Poole, Darren L.

AU - Leach, Stuart G.

AU - Parkinson, John A.

AU - Tuttle, Tell

AU - Murphy, John A.

PY - 2020/4/14

Y1 - 2020/4/14

N2 - 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

AB - 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

KW - N-Arylindoles

KW - Grubbs-Stoltz reagent

KW - dihydroacridines

U2 - 10.1039/D0SC00361A

DO - 10.1039/D0SC00361A

M3 - Article

SN - 2041-6520

VL - 11

SP - 3719

EP - 3726

JO - Chemical Science

JF - Chemical Science

IS - 14

ER -

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

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