Domino N‐/C‐Arylation via In Situ Generation of a Directing Group: Atom‐Efficient Arylation Using Diaryliodonium Salts
- 7 April 2017
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 56 (19), 5263-5266
- https://doi.org/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
Funding Information
- Engineering and Physical Sciences Research Council
This publication has 45 references indexed in Scilit:
- Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium saltsBeilstein Journal of Organic Chemistry, 2013
- Autocatalysis for C–H Bond Activation by Ruthenium(II) Complexes in Catalytic Arylation of Functional ArenesJournal of the American Chemical Society, 2011
- Room Temperature, Metal-Free Synthesis of Diaryl Ethers with Use of Diaryliodonium SaltsOrganic Letters, 2011
- C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) SystemsAngewandte Chemie-International Edition, 2010
- C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) SystemsAngewandte Chemie, 2010
- Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl IodidesThe Journal of Organic Chemistry, 2008
- Ruthenium(IV)-Alkylidene als Katalysatorvorstufen für direkte Arylierungen von Alkenen mit Chlorarenen und eine Anwendung auf die sequenzielle KatalyseAngewandte Chemie, 2007
- The Ru(cod)(cot)-Catalyzed Alkenylation of Aromatic C−H Bonds with Alkenyl AcetatesJournal of the American Chemical Society, 2007
- Katalytische Arylierungen über C‐H‐Bindungsaktivierung mit AryltosylatenAngewandte Chemie, 2006
- Alkenyliodonium saltsRussian Chemical Reviews, 2000