3 years ago

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

Ruthenium-Catalyzed para-Selective C−H Alkylation of Aniline Derivatives
Jamie A. Leitch, Yunas Bhonoah, Mary F. Mahon, Claire L. McMullin, Andrew J. Paterson, Christopher G. Frost
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. Para-normal activity: The para-selective C−H alkylation of aniline derivatives is reported. The methodology is proposed to proceed by a dual role ruthenium process: cycloruthenation at N−H and redox radical generation. This strategy leads to para-selective alkylations using pyrimidine and quinazoline auxiliaries.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708961

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