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

Chemistry. 2024 Apr 21:e202400337. doi: 10.1002/chem.202400337. Online ahead of print.ABSTRACTA 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.PMID:38644351 | DOI:10.1002/chem.202400337

Source: Chemistry - April 21, 2024 Category: Chemistry Authors: Prabhakar K Pandey Moumita Patra Prabodh Ranjan Nilay Kumar Pal Sanjay Choudhary Jitendra K Bera Source Type: research