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Issue 22, 2017
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Ruthenium(ii)-catalyzed ortho-C–H arylation of diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination

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Abstract

We report the first method for the direct, regioselective Ru(II)-catalyzed oxidative arylation of C–H bonds in diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination. The reaction takes advantage of the attractive features of organosilanes as coupling partners, providing proof of concept for N-directed Ru(II)-catalyzed C–H arylation. This novel, operationally-simple and versatile protocol utilizes the Ru(II)/CuF2 reagent system in which CuF2 serves as a dual activator/oxidant in non-coordinating solvents to accommodate for ligand N-coordination. This first Ru(II)-catalyzed N-directed Hiyama C–H arylation offers broad implications to achieve numerous C–H bond functionalizations by versatile ruthenium(II) catalysis manifold.

Graphical abstract: Ruthenium(ii)-catalyzed ortho-C–H arylation of diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination

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Supplementary files

Article information


Submitted
01 Apr 2017
Accepted
11 Apr 2017
First published
25 Apr 2017

Org. Biomol. Chem., 2017,15, 4783-4788
Article type
Communication

Ruthenium(II)-catalyzed ortho-C–H arylation of diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination

P. Nareddy, F. Jordan and M. Szostak, Org. Biomol. Chem., 2017, 15, 4783
DOI: 10.1039/C7OB00818J

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