Rhodium-Catalyzed 1,4-Aryl Rearrangement of Sulfur Ylide for the Synthesis of 2-Pyridyl Thioethers
Jie Wang, Qingyang Li, Shanshan Wang, Xin‐Yan Wu, Xingguang Li, Pei Nian Liu
Abstract
We report a novel rhodium-catalyzed rearrangement involving N-substituted 2-thiopyridones and diazoesters. This reaction proceeds through the rhodium-catalyzed formation of sulfur ylides, followed by a direct C-N bond cleavage to achieve N-to-C 1,4-pyridyl migration. The protocol can be used to construct various thiopyridines possessing tetrasubstituted carbon stereocenters in moderate to excellent yields, which expands the transformation pattern of sulfur ylide intermediates in rearrangement reactions.
Topics & Concepts
YlideChemistryRhodiumStereocenterArylCatalysisSulfurMedicinal chemistryBond cleavageCleavage (geology)Organic chemistryEnantioselective synthesisAlkylGeotechnical engineeringEngineeringFracture (geology)Cyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods