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Cesium-Fluoride-Promoted Synthesis of Stable Organocesium Reagents and Their Ambident Reactivities with Arynes
Authors:Suhail A. Rather  Dr. S. Athimoolam  Dr. Qazi Naveed Ahmed
Affiliation:1. Natural Product and Medicinal Chemistry Division, Indian Institute of Integrative Medicine (CSIR-IIIM), 180001 Canal Road, Jammu, Jammu & Kashmir, India

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002 India;2. Department of Physics, University College of Engineering Nagercoil, Anna University of Technology Tirunelveli, Nagercoil, 629004 India;3. Natural Product and Medicinal Chemistry Division, Indian Institute of Integrative Medicine (CSIR-IIIM), 180001 Canal Road, Jammu, Jammu & Kashmir, India

Abstract:Described are the diverse reactivities of novel, stable, ambident thio-organocesium reagents (bearing electron withdrawing groups) against benzynes. Reactions at reflux temperature predominantly led to the generation of various functionalized stable sulfonium ylides and at 40 °C the same reaction underwent direct c-arylation. Furthermore, lack of internal hydrogen on the cesium reagent helped to produce different ortho-bifunctional arynes in both the reactions. Interestingly, depending on the reactivities of substrates, the one-pot tri-component procedure generated either ylides or σ-bond insertion products.
Keywords:stable compounds  thio-organocesium  ylides  σ-bond insertion  ortho-bifunctional arenes
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