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

Christopher J Teskey; Shariar M A Sohel; Danielle L Bunting; Sachin G Modha; Michael F Greaney

doi:10.1002/anie.201701523

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

Angew Chem Int Ed Engl. 2017 May 2;56(19):5263-5266. doi: 10.1002/anie.201701523. Epub 2017 Apr 7.

Authors

Christopher J Teskey¹, Shariar M A Sohel¹, Danielle L Bunting¹, Sachin G Modha¹, Michael F Greaney¹

Affiliation

¹ School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.

PMID: 28387054
DOI: 10.1002/anie.201701523

Abstract

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.

Keywords: C-H activation; N-heterocycles; arylation; iodonium compounds.

Publication types

Research Support, Non-U.S. Gov't