N‐Heterocyclic Carbene–Pd Polymers as Reusable Precatalysts for Cyanation and Ullmann Homocoupling of Aryl Halides: The Role of Solvent in Product Distribution. Issue 14 (1st July 2015)

• Record Type: Journal Article
• Authors: Karimi, Babak; Vafaeezadeh, Majid; Akhavan, Pari Fadavi
• Is Part Of: ChemCatChem. Volume 7:Issue 14(2015:Jul.)
• Page Start: 2248
• Page End: 2254
• Publication Date: 2015-07-01
• Subjects: Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201500383
• Languages: English
• ISSNs: 1867-3880

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A main‐chain N‐heterocyclic carbene (NHC) polymer with <italic>N</italic>‐dodecyl‐substituted groups was found to be a highly efficient precatalyst for cyanation of various aryl halides by using nontoxic cyanic source [K₄Fe(CN)₆] under relatively mild reaction conditions. Several aryl iodides, bromides, and activated chlorides were successfully converted to their corresponding benzonitrile derivatives without using additives (such as reducing agents or exogenous organic ligands) in good to excellent yields. Our investigations showed that changing the solvent from DMF to polyethylene glycol (PEG‐200) resulted in dramatic decline of cyanation product formation to the benefit of the Ullmann homocoupling reaction. The catalyst could be reused four and five times with only slight loss of activity in cyanation and the Ullmann coupling, respectively.</p> </abstract>