Dual Gold/Silver Catalysis: Indolizines from 2-Substituted Pyridine Derivatives via a Tandem C(sp<sup>3</sup>)–H Alkynylation/Iminoauration
Chunyu Han, Yaowen Liu, Xianhai Tian, Frank Röminger, A. Stephen K. Hashmi
Abstract
A dual gold/silver-catalyzed cascade C(sp3)–H alkynylation/iminoauration of 2-substituted pyridines with hypervalent iodine(III) reagents for the synthesis of indolizines is described. This novel reaction involves the formation of an alkynyl Au(III) species, a dual gold/silver-catalyzed C(sp3)–H functionalization, and a subsequent iminoauration process. A number of indolizines bearing diverse functionalities were prepared in good to excellent yield. Furthermore, a gram-scale reaction was efficiently conducted.
Topics & Concepts
ChemistryHypervalent moleculeCatalysisReagentPyridineYield (engineering)Cascade reactionCombinatorial chemistryTandemSurface modificationIodineOrganic chemistryMetallurgyPhysical chemistryComposite materialMaterials scienceSynthesis and Reactivity of HeterocyclesCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions