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Photoredox/Copper-Catalyzed Enantioselective S-Alkylation of Sulfenamides with Hydrocarbons Enabled by Commercial BOX Ligands
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DOI：10.1021/acscatal.6c04310.png)
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Abstract
En 中文
Enantioenriched sulfilimines are valuable sulfur-stereogenic building blocks, but catalytic asymmetric S-alkylation directly from hydrocarbons is still challenging. Here we report a dual photoredox/copper-catalyzed enantioselective S-alkylation of N-acyl sulfenamides with hydrocarbons enabled by commercially available chiral bis(oxazoline) (BOX) ligands. The reaction merges peroxide-based HAT with chiral copper catalysis to furnish sulfur-stereogenic sulfilimines from benzylic hydrocarbons and representative unactivated alkanes in good yields and enantioselectivities (up to 90% ee). A practical feature is that the hydrocarbon coupling partner is typically used in only 10 equivalents, improving substrate economy compared with related radical C(sp3)–H functionalizations. Stern–Volmer studies show efficient quenching of the photocatalyst by a copper/BOX/sulfenamide assembly, consistent with a cooperative initiation pathway.
Keywords:
Alkyls
Aromatic compounds
Functionalization
Hydrocarbons
Ligands
C–H activation
copper-catalysis
enantioselective S-alkylation
sulfilimines
radical process
Journal
IF:
13.1
Papers:
1.6W
Citations:
15.0W
Organization
Cited Papers