Sustainable hydration of alkynes promoted by first row transition metal complexes. Background, highlights and perspectives

Atom-economic synthesis of β-ketosulfones based on gold-catalyzed highly regioselective hydration of alkynylsulfones

“…Although Hg II -based species demonstrate a high ability to activate the CuC π-system toward the nucleophilic addition, their application is strongly limited by the extreme toxicity of mercury-containing species. Various Brønsted and Lewis acids have also been employed for the hydration 24,25,35,36 as alternative activators.…”

“…Moreover, catalysis, which is the most important pillar of green chemistry, is widely used to increase the efficiency of hydration of alkynes. 24,25 Another benefit of this reaction is the employment of water as one of the most inexpensive and environmentally benign sources of oxygen. β-Ketosulfones can be represented as formal hydrates of alkynylsulfones, however, only a few cases of the hydration of specific alkynylsulfones leading to β-ketosulfones have been reported and no comprehensive study of this reaction was conducted up to date.…”

Fabrication of Flexible Co‐salen Integrated Polymers for Hydration of Epoxides and Alkynes via Cooperative Activation

“…Markovnikov hydration of alkynes is of particular importance in organic synthetic chemistry since the resulting valueadded ketones for both the bulk and fine chemical industries. [48][49][50][51][52] Traditional catalytic system always includes mercury(II) salts and strong acid, however, the toxicity of mercury impedes the practical application. Recently, non-precious cobalt complexes, such as porphyrin-Co(III) [51] and Co IIIsalen [53,54] have shown good activity in the hydration of alkynes.…”

Cyclic vs. acyclic alkyne towards Hg2+ ion detection: combined experimental and theoretical studies

“…This structural contrast is expected to create a difference in reactivity in terminal and internal alkynes. There are some reactions where both the terminal and internal alkynes participate similarly, [43][44][45][46] while there are others that are specific only for terminal alkynes such as reaction with a base or alkyne-alkyne coupling reactions. [47][48][49] However, to unambiguously compare the differences in reactivity between terminal and internally conjugated alkynes, their basic molecular platform must be same, only varying the alkyne positions.…”