Recyclable Polymer-Supported Terpyridine–Palladium Complex for the Tandem Aminocarbonylation of Aryl Iodides to Primary Amides in Water Using NaN3 as Ammonia Equivalent
Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Nishihara, Okinawa 903-0213, Japan
Author to whom correspondence should be addressed.
Catalysts 2017, 7(4), 107; https://doi.org/10.3390/catal7040107
Received: 17 March 2017 / Revised: 3 April 2017 / Accepted: 5 April 2017 / Published: 7 April 2017
(This article belongs to the Special Issue Organometallic Catalysis for Organic Synthesis)
Primary aromatic amides are valuable compounds, which are generally prepared via Beckmann rearrangement of oximes and the hydration of nitriles in organic solvents. We investigated the environmentally friendly catalytic aminocarbonylation in water. Thus, a novel heterogeneous transition-metal catalyst, a polymer-supported terpyridine–palladium(II) complex, was prepared and found to promote azidocarbonylation of aryl iodides with NaN3 and to reduce the generated benzoyl azides in water under CO gas to yield primary aryl amides with high to excellent yield in a one-pot reaction. The catalyst was recovered and reused several times with no loss of catalytic activity.