Hydropersulfide (RSSH)-Mediated Hydrothiolation of Alkenes.
Jeffrey Ash1, Kevin Curtis2, Shishir Bhowmik1
1Department of Chemistry and Biochemistry, University of Nevada Las Vegas, 4505 South Maryland Parkway, Las Vegas, Nevada 89154-4003, United States.
The Journal of Organic Chemistry
|January 3, 2025
Summary
A novel hydrothiolation reaction enables carbon-sulfur bond formation in alkenes using hydropersulfides. This efficient, metal-free method proceeds under mild conditions with Markovnikov selectivity.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Carbon-sulfur (C-S) bond formation is crucial in organic synthesis.
- Developing efficient and selective methods for C-S bond formation remains an active area of research.
Purpose of the Study:
- To develop a novel hydropersulfide-mediated hydrothiolation reaction for C-S bond formation.
- To achieve Markovnikov selectivity in the hydrothiolation of alkenes.
- To establish a transition-metal-, additive-, and solvent-free reaction under mild conditions.
Main Methods:
- Hydrothiolation of alkenes using hydropersulfides.
- Control experiments to investigate reaction mechanism.
- Density functional theory (DFT) calculations to support mechanistic proposals.
Main Results:
- Successful development of a hydropersulfide-mediated hydrothiolation reaction.
- Achieved Markovnikov selectivity in the C-S bond formation.
- The reaction proceeds under mild, metal-free, additive-free, and solvent-free conditions.
- Elemental sulfur is released during the reaction.
Conclusions:
- A new, efficient, and environmentally benign method for C-S bond formation has been established.
- The reaction mechanism is proposed to be ionic, involving the release of elemental sulfur.
- This methodology offers a valuable tool for synthesizing sulfur-containing organic compounds.
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