2024
DOI: 10.1002/chem.202400363
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TBADT‐Mediated Photocatalytic Stereoselective Radical Alkylation of Chiral N‐Sulfinyl Imines: Towards Efficient Synthesis of Diverse Chiral Amines

Matteo Leone,
Joseph P. Milton,
Dorota Gryko
et al.

Abstract: Herein we describe a sustainable and efficient photocatalytic method for the stereoselective radical alkylation of chiral sulfinyl imines. By employing readily available non‐prefunctionalized radical precursors and low loading of TBADT as a direct HAT photocatalyst, we successfully obtain diverse chiral amines with high yields and excellent diastereoselectivity under mild conditions. This method provides an efficient approach for accessing a diverse array of medicinally relevant compounds, including both natur… Show more

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Cited by 10 publications
(1 citation statement)
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“…1 DT in a solution containing organic substrates could be easily reduced with appearance of blue color when irradiated with UV light, which signified its potential to act as a promising photocatalyst. 2,3 Recently, the decatungstate anion has attracted growing attention due to its outstanding photocatalytic performance in various reactions, including activation of inert C(sp 3 )–H bonds via hydrogen atom transfer (HAT) or single electron transfer (SET), 4–6 oxidation of organic substrates, 7–11 degradation of organic pollutants, 12,13 etc. However, commonly used DT-based photocatalytic catalysts, such as (Bu 4 N) 4 [W 10 O 32 ] (TBADT) and Na 4 [W 10 O 32 ] (NaDT), were known to have a relatively low light harvesting efficiency.…”
Section: Introductionmentioning
confidence: 99%
“…1 DT in a solution containing organic substrates could be easily reduced with appearance of blue color when irradiated with UV light, which signified its potential to act as a promising photocatalyst. 2,3 Recently, the decatungstate anion has attracted growing attention due to its outstanding photocatalytic performance in various reactions, including activation of inert C(sp 3 )–H bonds via hydrogen atom transfer (HAT) or single electron transfer (SET), 4–6 oxidation of organic substrates, 7–11 degradation of organic pollutants, 12,13 etc. However, commonly used DT-based photocatalytic catalysts, such as (Bu 4 N) 4 [W 10 O 32 ] (TBADT) and Na 4 [W 10 O 32 ] (NaDT), were known to have a relatively low light harvesting efficiency.…”
Section: Introductionmentioning
confidence: 99%