The Applications of Water as Reagents in Organic Synthesis

Abstract

Summary In recent years, water, as one of the most inexpensive and environmentally benign solvents, has been extensively investigated as a versatile reagent for the rapid introduction of hydrogen atom, oxygen atom, or hydroxyl group into the target product. Furthermore, with regard to enormous enzyme-catalyzed biosynthesis in nature, water serves as a favorable medium for the versatile synthesis of a variety of complicated molecules and compounds. This chapter discusses the following four parts: incorporation of hydrogen atom from water; incorporation of oxygen atom from water; incorporation of hydroxyl group from water; and traceless promotion of the reactions by water. The observation data of control experiments implied that the residual water in the DMSO played the critical role in the reaction. The initial step of the plausible pathway involved the generation of silver acetylide. Under the promotion of a trace amount of H2O in the DMSO solvent, the protonation of vinyl silver released the final product.