Synthesis of 3-thiocyanated chromones via TCCA/NH4SCN-mediated cyclization/thiocyanation of alkynyl aryl ketones
Jiaxi Xiao, Zhenkang Ai, Xuemin Li, Sanqing Tao, Bingyue Zhao, Xiaofan Wang, Xiaofan Wang, Xinbo Wang, Xinbo Wang, Yunfei Du
Abstract
3-Thiocyanated chromones was conveniently synthesized from alkynyl aryl ketones using commercially available, inexpensive trichloroisocyanuric acid (TCCA) as oxidant and NH4SCN as thiocyanato (SCN) source. This metal-free approach is postulated to first in situ generate thiocyanogen chloride (Cl-SCN) from the reaction of TCCA and NH4SCN, followed by a rare efficient electrophilic thiocyano oxyfunctionalization of alkynes enabled by the reactive electrophilic species generated thereof.
Topics & Concepts
ElectrophileTrichloroisocyanuric acidChemistryArylChlorideCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalysisAlkylSulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsSynthesis of Organic Compounds