1,2-Difunctionalization of Aryne with Sulfenamide and Organohalide: Mild and Metal-Free Access to <i>S</i>-(<i>o</i>-Halo)aryl Sulfilimine
Padma Priya V. R., Antony Haritha Mercy A, Natarajan K, S. Ravindra, Ganesh Chandra Nandi
Abstract
A mild and metal-free approach has been developed for 1,2-difunctionalization of aryne using sulfenamides as a nucleophile and a halogen source (CX 4 ) as an electrophile to synthesize S -( o -halo)aryl sulfilimines. The late-stage functionalizations of halide handles via Suzuki–Miyaura and Buchwald–Hartwig reactions exhibit the synthetic utilities of the products. The chemoselectivity, regioselectivity, rapidity, and use of economical CCl 4 are the advantages of this protocol.
Topics & Concepts
AryneChemistryRegioselectivityElectrophileNucleophileArylChemoselectivityCombinatorial chemistryHalogenOrganic chemistryComputational chemistryMedicinal chemistryCatalysisAlkylCyclization and Aryne ChemistryCatalytic Alkyne ReactionsChemical synthesis and alkaloids