Bio-inspired Halogen Bonding-Promoted Cross Coupling for the Synthesis of Organoselenium Compounds

Bo Li, Liang Yi, Bholanath Maity, Jiaqi Jia, Yuqin Shen, Xiang Yu Chen*, Luigi Cavallo*, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Noncovalent interactions play fundamental roles in many organic and biochemical processes, including hydrogen and halogen bonding, which are vital in the fields of synthesis and catalysis. Herein, we describe the application of halogen bonding interactions to facilitate the reaction balance between an electron donor-acceptor (EDA) complex and Ph2Se2 for the synthesis of a series of organoselenium compounds. The EDA complex concept has recently emerged as an attractive path for visible light-induced transformations due to facile reaction conditions and the avoidance of photocatalysts. Density functional theory calculations reveal that an iodine-π* interaction leads to the formation of an alkyl radical from the N-(acyloxy)phthalimide ester. The resulting alkyl radical is captured by the diselenide-I• complex to form the C-Se bond. The developed selenide synthesis strategy has been applied in the transformation of primary, secondary, and tertiary carboxylic acids as well as a series of natural products, drugs, and α-selenoamino acids.

Original languageEnglish (US)
Pages (from-to)15194-15202
Number of pages9
JournalACS Catalysis
Volume13
Issue number22
DOIs
StatePublished - Nov 17 2023

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

Keywords

  • amino acid
  • chalcogen
  • EDA complex
  • halogen bonding
  • late-stage functionalization
  • organoselenium compounds
  • photochemistry
  • photoredox catalysis

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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