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

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

16 Downloads (Pure)

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

Access to Document

10.1039/D0SC00361ALicence: CC BY 3.0

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

Cite this

Smith, A. J., Dimitrova, D., Arokianathar, J. N., Kolodziejczak, K., Young, A., Allison, M., Poole, D. L., Leach, S. G., Parkinson, J. A., Tuttle, T., & Murphy, J. A. (2020). New reductive rearrangement of N-Arylindoles triggered by the Grubbs-Stoltz reagent Et3SiH/KOtBu. Chemical Science, 11(14), 3719-3726. Advance online publication. https://doi.org/10.1039/D0SC00361A

@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",

}

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

Abstract

Keywords

Access to Document

Fingerprint

Cite this