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β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOF

Matloubi Moghaddam, F ; Sharif University of Technology | 2023

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  1. Type of Document: Article
  2. DOI: 10.1038/s41598-023-49670-5
  3. Publisher: Nature Research , 2023
  4. Abstract:
  5. Herein, the one-pot tandem synthesis of β-ketoallylic methylsulfones has been achieved from readily available dimethyl sulfoxide and acetophenones as coupling partners in one step. In this procedure, dimethyl sulfoxide serves as a triple role including solvent, dual synthon and as an oxidant agent. The use of magnetic Ag–Cu MOF as a bimetallic catalyst is the key to the progress of the reaction due to its accessible active sites. It provides facile access to various β-ketoallylic methylsulfone derivatives from direct C(sp 3)–H bond activation and functionalization of aromatic methyl ketones especially acetophenones with electron-rich and electron-poor groups. Moreover, the present work offers a synthetically powerful strategy to form products in good to excellent yields (74–96%) with the atom, step, and pot economics. It has also delivered a new chromane-4-one derivative from 2-hydroxy acetophenone with intramolecular Michael-addition of related β-ketoallyl methylsulfone product. In the final step, the electronic properties of some products have been predicted with the theoretical studies. © 2023, The Author(s)
  6. Keywords:
  8. Source: Scientific Reports ; Volume 13, Issue 1 , 2023 ; 20452322 (ISSN)
  9. URL: https://www.nature.com/articles/s41598-023-49670-5