Ru-Catalysed C-H Silylation of Unprotected Gramines, Tryptamines and their Congeners

Paul Gates; Karthik Devaraj; Carina Sollert; C. Juds; Lukasz T. Pilarski

doi:10.1039/C6CC00803H

Ru-Catalysed C-H Silylation of Unprotected Gramines, Tryptamines and their Congeners

Paul Gates, Karthik Devaraj, Carina Sollert, C. Juds, Lukasz T. Pilarski

School of Chemistry

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Abstract

Selective Ru-catalysed C2-H silylation of heteroarenes is presented. The transformation works with or without directing group assistance and requires no protecting groups. Gramines and tryptamines may be converted efficiently whilst avoiding deleterious elimination side-reactions. Mechanistic studies reveal an unusual activation of the indole C4-H bond by an electron-rich metal.

Original language	English
Pages (from-to)	5868-5871
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	34
Early online date	1 Apr 2016
DOIs	https://doi.org/10.1039/C6CC00803H
Publication status	Published - 30 Apr 2016

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via RSC at http://pubs.rsc.org/en/Content/ArticleLanding/2016/CC/C6CC00803H#!divAbstract. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 1.18 MB

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title = "Ru-Catalysed C-H Silylation of Unprotected Gramines, Tryptamines and their Congeners",

abstract = "Selective Ru-catalysed C2-H silylation of heteroarenes is presented. The transformation works with or without directing group assistance and requires no protecting groups. Gramines and tryptamines may be converted efficiently whilst avoiding deleterious elimination side-reactions. Mechanistic studies reveal an unusual activation of the indole C4-H bond by an electron-rich metal.",

author = "Paul Gates and Karthik Devaraj and Carina Sollert and C. Juds and Pilarski, {Lukasz T.}",

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T1 - Ru-Catalysed C-H Silylation of Unprotected Gramines, Tryptamines and their Congeners

AU - Gates, Paul

AU - Devaraj, Karthik

AU - Sollert, Carina

AU - Juds, C.

AU - Pilarski, Lukasz T.

PY - 2016/4/30

Y1 - 2016/4/30

N2 - Selective Ru-catalysed C2-H silylation of heteroarenes is presented. The transformation works with or without directing group assistance and requires no protecting groups. Gramines and tryptamines may be converted efficiently whilst avoiding deleterious elimination side-reactions. Mechanistic studies reveal an unusual activation of the indole C4-H bond by an electron-rich metal.

AB - Selective Ru-catalysed C2-H silylation of heteroarenes is presented. The transformation works with or without directing group assistance and requires no protecting groups. Gramines and tryptamines may be converted efficiently whilst avoiding deleterious elimination side-reactions. Mechanistic studies reveal an unusual activation of the indole C4-H bond by an electron-rich metal.

U2 - 10.1039/C6CC00803H

DO - 10.1039/C6CC00803H

M3 - Article (Academic Journal)

SN - 1359-7345

VL - 52

SP - 5868

EP - 5871

JO - Chemical Communications

JF - Chemical Communications

IS - 34

ER -

Ru-Catalysed C-H Silylation of Unprotected Gramines, Tryptamines and their Congeners

Abstract

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