A Single Terminal [NiII−OH] Catalyst for Direct Julia‐Type Olefination and α‐Alkylation Involving Sulfones and Alcohols

A terminal [NiII−OH] complex 1, supported by triflamide‐functionalized NHC ligands, showed divergent reactivity for the reaction of sulfone with alcohol, contingent on base concentration, temperature, and time. Julia‐type olefination of alcohols with sulfones was achieved using one equiv. of base, w...

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Published in:Chemistry : a European journal 2024-06, Vol.30 (35), p.e202400337-n/a
Main Authors: Pandey, Prabhakar K., Patra, Moumita, Ranjan, Prabodh, Kumar Pal, Nilay, Choudhary, Sanjay, Bera, Jitendra K.
Format: Article
Language:English
Subjects:
Alcohols
Alkylation
Biological activity
Borrowing-hydrogenation
Catalysts
Nickel
Olefination
Piceatannol
Pinosylvin
Resveratrol
Stilbene
Substrates
Sulfones
α-Alkylation
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Summary:A terminal [NiII−OH] complex 1, supported by triflamide‐functionalized NHC ligands, showed divergent reactivity for the reaction of sulfone with alcohol, contingent on base concentration, temperature, and time. Julia‐type olefination of alcohols with sulfones was achieved using one equiv. of base, whereas lowering base loading to 0.5 equiv. afforded α‐alkylated sulfones. Besides excellent substrate scope and selectivity, biologically active stilbene derivatives DMU‐212, pinosylvin, resveratrol, and piceatannol were synthesized in high yield under Julia‐type olefination conditions. An extensive array of controlled experiments and DFT calculations provide valuable insight on the reaction pathway. A single terminal [NiII−OH] catalyst is employed for direct Julia‐type olefination of alcohols and α‐alkylation of sulfones using different reaction conditions. Detailed mechanistic studies, including DFT calculations, are undertaken to gain insight on the reaction pathway.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202400337