Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
Tristan Delcaillau, Philip Boehm, Bill Morandi
Abstract
We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.
Topics & Concepts
ChemistryArylFunctional groupMetathesisCatalysisDerivatizationNickelCombinatorial chemistryCyanideNitrileSalt metathesis reactionCyanationOrganic chemistryAlkylHigh-performance liquid chromatographyPolymerizationPolymerSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsSynthetic Organic Chemistry Methods