120th General Meeting of the KCS

Type Symposium
Area [IBS Symposium] Developing New Catalytic Organic Reactions and Investigating Their Applications
Room No. Room 211+212+213
Time WED 15:20-:
Code KCS3-2
Subject Decarboxylative C-H Activation for the synthesis of homoisoflavonoids & Decarboxylative trichlorination
Authors Sunwoo Lee
Department of Chemistry, Chonnam National University, Korea
Abstract The development of simple and convenient method for the preparation of aryl alkynoic acids made it easy accessible tool for the introduction of alkynyl group in organic synthesis. In this presentation, we would like to discuss some of our recent research progress towards the decarboxylative coupling reactions of alkynoic acids. This presentation will cover the ruthenium-catalyzed decarboxylative C-H activation for the synthesis of homoisofalvonoids and metal-free decarboxylative trichlorination of alkynoic acid for the synthesis of trichloromethylketones. Homoisoflavonoid and flavone were selectively obtained from the reaction with salicylaldehydes and arylpropiolic acid in the presence of ruthenium catalyst and base. When the reaction was conducted in DMSO, a variety of homoisoflavonoids were exclusively obtained in good yields. While, several flavones were dominantly formed under t-AmOH solvent. 2,2,2-Trichloroacetophenone derivatives were synthesized via decarboxylative trichlorination from arylpropiolic acids and trichloroisocyanuric acid (TCCA). The reaction was conducted in the presence of H2O at room temperature, and afforded the desired products in good yields. The reaction showed good functional group tolerance towards halides, cyano, nitro, ketone, ester and aldehyde groups. In addition, 2,2,2-trichloroacetophenone derivatives were readily transformed into esters, amides, and hydrazides.
E-mail sunwoo@chonnam.ac.kr