Light-Mediated Sulfur-Boron Exchange
Liubov I Panferova1, Alexander D Dilman1
1N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation.
Organic Letters
|April 30, 2021
Summary
A new photocatalytic method enables the synthesis of pinacol boronic esters from sulfides using an organic photocatalyst (3DPA2FBN) and 400 nm light. This versatile reaction efficiently converts primary, secondary, and tertiary sulfides.
Area of Science:
- Organic Chemistry
- Photocatalysis
- Synthetic Methodology
Background:
- Boronic esters are versatile synthetic intermediates.
- Developing efficient methods for their synthesis is crucial.
- Photocatalysis offers a sustainable approach to organic transformations.
Purpose of the Study:
- To develop a novel photocatalytic method for synthesizing pinacol boronic esters.
- To explore the use of sulfides as starting materials in this transformation.
- To investigate the role of photocatalyst structure in reaction efficiency.
Main Methods:
- Reaction of sulfides with bis(catecholato)diboron.
- Photocatalysis using 3,5-bis(2,4,6-tris(benzyloxy)phenyl)hexafluorobiphenyl (3DPA2FBN) under 400 nm irradiation.
- Subsequent treatment with pinacol and triethylamine.
Main Results:
- Efficient synthesis of pinacol boronic esters from primary, secondary, and tertiary sulfides.
- The electron-deficient tetrafluoropyridinyl group is key to generating alkyl radicals.
- The reaction proceeds under mild conditions with good yields.
Conclusions:
- A novel and efficient photocatalytic route to pinacol boronic esters from sulfides has been established.
- This method offers a valuable tool for organic synthesis.
- The study highlights the importance of photocatalyst design and substrate electronic properties.
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