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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Micelle-Enabled One-Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III)
Jakkrit Srisa1,2, Theeranon Tankam1, Mongkol Sukwattanasinitt1,3
1Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
Abstract:
In this work, we developed a one-pot synthesis of guanidine directly from isothiocyanate using DIB (diacetoxyiodobenzene) as a desulfurizing agent under micellar conditions in water. Our optimization study revealed that the use of 1 % TPGS-750-M as a surfactant with NaOH as an additive base at room temperature can convert a variety of isothiocyanates and amines into corresponding guanidines in excellent yields (69-95 %). This synthetic process in water can be applied to prepare guanidine at gram-scale quantity. Our aqueous micellar medium also demonstrated high reusability as the reaction can be performed for several cycles without losing its efficiency. The reaction is metal-free, utilizes water as solvent and practical (room temperature and open flask).
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