Room Temperature C–H Arylation of Benzofurans by Aryl Iodides
- 2 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7079-7082
- https://doi.org/10.1021/acs.orglett.1c02397
Abstract
A robust method of room temperature direct arylation for benzofuran is reported. This discovery allows for mild arylation by commercially available aryl iodides with complete C-2 regioselectivity and tolerates a range of functional groups, including heat sensitive groups. Mechanistically, a Heck-type oxyarylation product from a direct arylation process is reported as a key piece of evidence for a carbopalladation intermediate.Keywords
Funding Information
- Clean Energy Institute
- Center for Selective C-H Functionalization, National Science Foundation (CHE-1700982)
This publication has 34 references indexed in Scilit:
- Combined Oxypalladation/C-H Functionalization: Palladium(II)‐Catalyzed Intramolecular Oxidative Oxyarylation of HydroxyalkenesAngewandte Chemie, 2012
- Analysis of the Palladium-Catalyzed (Aromatic)C–H Bond Metalation–Deprotonation Mechanism Spanning the Entire Spectrum of ArenesThe Journal of Organic Chemistry, 2011
- 2-Arylbenzofuran, Flavonoid, and Tyrosinase Inhibitory Constituents of Morus yunnanensisJournal of Natural Products, 2011
- Mechanistic Origin of Ligand‐Controlled Regioselectivity in Pd‐Catalyzed C-H Activation/Arylation of ThiophenesChemistry – A European Journal, 2011
- Room Temperature and Phosphine Free Palladium Catalyzed Direct C-2 Arylation of IndolesJournal of the American Chemical Society, 2008
- C−C Bond Formation via Double C−H Functionalization: Aerobic Oxidative Coupling as a Method for Synthesizing Heterocoupled BiarylsOrganic Letters, 2007
- Friedel–Crafts acylation of aromatics and heteroaromatics by beta zeoliteJournal of Molecular Catalysis A: Chemical, 2005
- Influence of building block aromaticity in the determination of electronic properties of five-membered heterocyclic oligomersPhysical Chemistry Chemical Physics, 2002
- To What Extent Can Aromaticity Be Defined Uniquely?The Journal of Organic Chemistry, 2002
- Aromaticity and Antiaromaticity in Five‐Membered C4H4X Ring Systems: “Classical” and “Magnetic” Concepts May Not Be “Orthogonal”Angewandte Chemie, 1995