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

Autor: Pandey PK; Department of Chemistry and Centre for Environmental Sciences and Engineering, Indian Institute of Technology Kanpur, Kanpur, 208016, India., Patra M; Department of Chemistry and Centre for Environmental Sciences and Engineering, Indian Institute of Technology Kanpur, Kanpur, 208016, India., Ranjan P; Department of Chemistry and Centre for Environmental Sciences and Engineering, Indian Institute of Technology Kanpur, Kanpur, 208016, India., Kumar Pal N; Department of Chemistry and Centre for Environmental Sciences and Engineering, Indian Institute of Technology Kanpur, Kanpur, 208016, India., Choudhary S; Department of Chemistry and Centre for Environmental Sciences and Engineering, Indian Institute of Technology Kanpur, Kanpur, 208016, India., Bera JK; Department of Chemistry and Centre for Environmental Sciences and Engineering, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Jun 20; Vol. 30 (35), pp. e202400337. Date of Electronic Publication: 2024 May 22.
DOI: 10.1002/chem.202400337
Abstrakt: A terminal [Ni II -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.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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