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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Delta-sultone formation through Rh-catalyzed C-H insertion.
Scott A Wolckenhauer1, A Sloan Devlin, J Du Bois
1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Organic Letters
|September 25, 2007
Summary
This study presents a general method for synthesizing delta-sultones using rhodium-catalyzed reactions. The approach utilizes diazo or iodonium ylide intermediates for efficient cyclization, enabling diverse applications in fine chemical synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Sulfonate ester derivatives are important precursors in organic synthesis.
- Rhodium-catalyzed reactions offer powerful tools for C-C and C-heteroatom bond formation.
- Delta-sultones are valuable heterocyclic compounds with applications in various chemical fields.
Purpose of the Study:
- To develop a general and efficient method for the synthesis of delta-sultones.
- To explore the use of rhodium-catalyzed 1,6-insertion reactions for assembling delta-sultones.
- To demonstrate the utility of the synthesized delta-sultones in fine chemical synthesis.
Main Methods:
- Rhodium-catalyzed cyclization of sulfonate ester derivatives.
- Utilizing diazo or iodonium ylide intermediates to generate rhodium-carbene species.
- Employing reductive and oxidative reactions for the subsequent transformation of delta-sultones.
Main Results:
- A general method for assembling delta-sultones via rhodium-catalyzed 1,6-insertion was established.
- Two distinct protocols were developed, leveraging the reactivity of diazo and iodonium ylide intermediates.
- The synthesized delta-sultones were effectively utilized in both reductive and oxidative transformations, allowing for the removal of the sulfonate group.
Conclusions:
- Rhodium-catalyzed reactions of sulfonate esters provide a versatile route to delta-sultones.
- The developed protocols offer efficient access to these important heterocycles.
- Delta-sultones serve as valuable intermediates in the synthesis of fine chemicals.
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