Tandem Catalytic C(sp(3) )-H Amination/Sila-Sonogashira-Hagihara Coupling Reactions with Iodine Reagents

Julien Buendia; Benjamin Darses; Philippe Dauban

doi:10.1002/anie.201412364

Tandem Catalytic C(sp(3) )-H Amination/Sila-Sonogashira-Hagihara Coupling Reactions with Iodine Reagents

Angew Chem Int Ed Engl. 2015 May 4;54(19):5697-701. doi: 10.1002/anie.201412364. Epub 2015 Mar 17.

Authors

Julien Buendia¹, Benjamin Darses, Philippe Dauban

Affiliation

¹ Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Avenue de la Terrasse, F-91198 Gif-sur-Yvette (France).

PMID: 25783616
DOI: 10.1002/anie.201412364

Abstract

A new tandem C-N and C-C bond-forming reaction has been achieved through Rh(II) /Pd(0) catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations.

Keywords: CH Activation; cross-coupling; homogeneous catalysis; hypervalent compounds; synthetic methods.