Insights into the Halogen Effects on Regioselectivities of Nucleophilic Haloalkylation of α,β‐Enones.

  • Published In: Chemistry - An Asian Journal, 2025, v. 20, n. 6. P. 1 1 of 3

  • Database: Academic Search Ultimate 2 of 3

  • Authored By: Zheng, Meng‐Meng; Rao, Zizhen; Sang, Yueqian; Shao, Qianzhen; Xu, Haoran; Xue, Xiao‐Song 3 of 3

Abstract

The halogen effects, specifically the replacement of chlorine with fluorine, on the shift in regioselectivity from 1,4‐ to 1,2‐addition in the nucleophilic haloalkylation of α,β‐enones have been investigated using density functional theory (DFT) calculations. Computational analysis revealed that the difluorocarbanion PhSO2CF2−, being a hard nucleophile with lower energy of the highest occupied molecular orbital (HOMO), selectively undergoes 1,2‐addition of chalcone, primarily dominated by Coulombic interactions. In contrast, the nucleophilic 1,4‐addition of chalcone by a soft dichlorocarbanion PhSO2CCl2− is controlled by frontier molecular orbital interactions. This work provides a deep understanding of the regioselective control in nucleophilic haloalkylation reactions. [ABSTRACT FROM AUTHOR]

Additional Information

  • Source:Chemistry - An Asian Journal. 2025/03, Vol. 20, Issue 6, p1
  • Document Type:Article
  • Subject Area:Chemistry
  • Publication Date:2025
  • ISSN:1861-4728
  • DOI:10.1002/asia.202500055
  • Accession Number:183820700
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