Ruthenium-Catalyzed para-Selective C−H Alkylation of Aniline Derivatives

Jamie A. Leitch, Claire L. Mcmullin, Andrew J. Paterson, Mary F. Mahon, Yunas Bhonoah, Christopher G. Frost

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Abstract

The para-selective C−H alkylation of aniline derivatives furnished with a pyrimidine auxiliary is herein reported. This reaction is proposed to take place via an N−H-activated cyclometalate formed in situ. Experimental and DFT mechanistic studies elucidate a dual role of the ruthenium catalyst. Here the ruthenium catalyst can undergo cyclometalation by N−H metalation (as opposed to C−H metalation in meta-selective processes) and form a redox active ruthenium species, to enable site-selective radical addition at the para position.
Original languageEnglish
Pages (from-to)15131-15135
Number of pages6
JournalAngewandte Chemie-International Edition
Volume56
Issue number47
Early online date2 Oct 2017
DOIs
Publication statusPublished - 20 Nov 2017

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Ruthenium
Alkylation
Oxidation-Reduction
aniline

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Ruthenium-Catalyzed para-Selective C−H Alkylation of Aniline Derivatives. / Leitch, Jamie A.; Mcmullin, Claire L.; Paterson, Andrew J.; Mahon, Mary F.; Bhonoah, Yunas; Frost, Christopher G.

In: Angewandte Chemie-International Edition, Vol. 56, No. 47, 20.11.2017, p. 15131-15135.

Research output: Contribution to journalArticle

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