We're investigating a series of reactions of thiols with alkynes. The reactions proceed via deprotonation of the thiol followed by a nucleophilic attack of the thiolate ion to the α-carbon atom of the triple bond. These reactions are performed in water and the pH is raised to 10 by addition of NaOH, since the pKa of thiols is around 9,5. It's a methodology focused research, we are not doing total synthesis of any kind.
Could NaOH be substituted with some organic base which is stable in water in order to deprotonate the thiol? Maybe some non-nucleophilic base, so it does not react with the alkyne?