Micelle-Enabled One-Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III) Reagents under Mild Conditions

Jakkrit Srisa; Theeranon Tankam; Mongkol Sukwattanasinitt; Sumrit Wacharasindhu

doi:10.1002/asia.201900982

Micelle-Enabled One-Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III) Reagents under Mild Conditions

Chem Asian J. 2019 Oct 1;14(19):3335-3343. doi: 10.1002/asia.201900982. Epub 2019 Sep 9.

Authors

Jakkrit Srisa^{1

2}, Theeranon Tankam¹, Mongkol Sukwattanasinitt^{1

3}, Sumrit Wacharasindhu^{2

3}

Affiliations

¹ Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
² Center of Excellence on Petrochemical and Materials Technology, Chulalongkorn University, Bangkok, Thailand.
³ Nanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.

PMID: 31397526
DOI: 10.1002/asia.201900982

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).

Keywords: guanidine; hypervalent iodine; one-pot synthesis; reactions in water; surfactants.

Abstract

Grants and funding