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

Autor:	Smith AJ; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk., Dimitrova D; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk., Arokianathar JN; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk., Kolodziejczak K; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk., Young A; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk., Allison M; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk., Poole DL; GlaxoSmithKline Medicines Research Centre Gunnels Wood Road, Stevenage SG1 2NY UK., Leach SG; GlaxoSmithKline Medicines Research Centre Gunnels Wood Road, Stevenage SG1 2NY UK., Parkinson JA; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk., Tuttle T; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk., Murphy JA; Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK john.murphy@strath.ac.uk tell.tuttle@strath.ac.uk.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2020 Mar 11; Vol. 11 (14), pp. 3719-3726. Date of Electronic Publication: 2020 Mar 11.
DOI:	10.1039/d0sc00361a
Abstrakt:	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. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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