3 years ago

Domino N-/C-Arylation via In Situ Generation of a Directing Group: Atom-Efficient Arylation Using Diaryliodonium Salts

Domino N-/C-Arylation via In Situ Generation of a Directing Group: Atom-Efficient Arylation Using Diaryliodonium Salts
Danielle L. Bunting, Shariar M. A. Sohel, Michael F. Greaney, Christopher J. Teskey, Sachin G. Modha
Both aryl components of diaryliodonium salts can be used in a domino one-pot reaction via in situ generation of a directing group. A number of heterocycles undergo N-arylation which is followed by ruthenium-catalyzed C-arylation. Notably the reaction extends well to unsymmetrical diaryliodonium salts with a number of highly selective examples shown. First the one, then the other: Diaryl- and alkenyl(aryl)iodonium salts react with N-heteroarenes in domino fashion. N-functionalization is followed by ortho-arylation under ruthenium catalysis, capturing the aryl iodide by-product of the first step.

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

DOI: 10.1002/anie.201701523

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