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Transition Metal Mediated Hydrolysis of C-S Bonds: An Overview of a New Reaction Strategy.
| Content Provider | Europe PMC |
|---|---|
| Author | Ganguly, Tuhin Chakraborty, Anuj Baran Majumdar, Amit |
| Copyright Year | 2023 |
| Description | Desulfurization of organosulfur substrates is highly important due to its relation with the industrial hydrodesulfurization (HDS) process of fossil fuels, which helps to eliminate the sulfur-containing impurities such as thiols, sulfide, thiophenes, etc. from crude oil for the production of easily processed and more cleanly combusted fuel with very low sulfur content. While the HDS process involves a hydrogenolysis reaction under a high pressure of hydrogen gas at high temperature, the hydrolysis of C–S bonds of organosulfur substrates at ambient conditions may very well be considered as a potential alternative for model desulfurization reactions. However, unlike the availability of an appreciable number of reports on base, acid, and metal ion mediated hydrolysis of thioesters in the literature, reports on the hydrolysis of more difficult substrates such as thiolates, sulfides, and other organosulfur substrates remained unavailable until 2017. The very recent discovery of a transition metal mediated hydrolysis reaction of C–S bonds at ambient conditions, however, has rapidly filled in this gap within the past few years. Development of this new stoichiometric reaction allowed the desulfurization of a large number of organosulfur substrates, including aliphatic and aromatic thiols, thiocarboxylic acids, sulfides, disulfides, thiophenes, and dibenzothiophene, at ambient conditions and was subsequently converted to a catalytic process for the hydrolysis of thiols. A brief overview of this new reaction strategy, a proposed reaction mechanism, a critical analysis of the efficiency, and future prospects are presented. |
| Abstract | Desulfurization oforganosulfur substrates is highly importantdue to its relation with the industrial hydrodesulfurization (HDS)process of fossil fuels, which helps to eliminate the sulfur-containingimpurities such as thiols, sulfide, thiophenes, etc. from crude oilfor the production of easily processed and more cleanly combustedfuel with very low sulfur content. While the HDS process involvesa hydrogenolysis reaction under a high pressure of hydrogen gas athigh temperature, the hydrolysis of C–S bonds of organosulfursubstrates at ambient conditions may very well be considered as apotential alternative for model desulfurization reactions. However,unlike the availability of an appreciable number of reports on base,acid, and metal ion mediated hydrolysis of thioesters in the literature,reports on the hydrolysis of more difficult substrates such as thiolates,sulfides, and other organosulfur substrates remained unavailable until2017. The very recent discovery of a transition metal mediated hydrolysisreaction of C–S bonds at ambient conditions, however, has rapidlyfilled in this gap within the past few years. Development of thisnew stoichiometric reaction allowed the desulfurization of a largenumber of organosulfur substrates, including aliphatic and aromaticthiols, thiocarboxylic acids, sulfides, disulfides, thiophenes, anddibenzothiophene, at ambient conditions and was subsequently convertedto a catalytic process for the hydrolysis of thiols. A brief overviewof this new reaction strategy, a proposed reaction mechanism, a criticalanalysis of the efficiency, and future prospects are presented. |
| Related Links | https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC10704582&blobtype=pdf |
| Volume Number | 3 |
| DOI | 10.1021/acsorginorgau.3c00038 |
| PubMed Central reference number | PMC10704582 |
| Issue Number | 6 |
| PubMed reference number | 38075449 |
| Journal | ACS Organic & Inorganic Au [ACS Org Inorg Au] |
| e-ISSN | 2694247X |
| Language | English |
| Publisher | American Chemical Society |
| Publisher Date | 2023-09-20 |
| Access Restriction | Open |
| Rights License | Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). © 2023 The Authors. Published by American Chemical Society |
| Subject Keyword | Desulfurization C−S bond cleavage hydrolysis thiol hydrolysis hydrosulfide transition metal HDS |
| Content Type | Text |
| Resource Type | Article |
| Subject | Physical and Theoretical Chemistry Inorganic Chemistry Organic Chemistry |
