Nickel- and Palladium-Catalyzed Cross-Coupling Reactions of Organostibines with Organoboronic Acids

Dejiang Zhang, Liyuan Le, Renhua Qiu, Wai Yeung Wong, Nobuaki Kambe

Research output: Journal article publicationJournal articleAcademic researchpeer-review

3 Citations (Scopus)

Abstract

A strategy for the formation of antimony-carbon bond was developed by nickel-catalyzed cross-coupling of halostibines. This method has been applied to the synthesis of various triaryl- and diarylalkylstibines from the corresponding cyclic and acyclic halostibines. This protocol showed a wide substrate scope (72 examples) and was compatible to a wide range of functional groups such as aldehyde, ketone, alkene, alkyne, haloarenes (F, Cl, Br, I), and heteroarenes. A successful synthesis of arylated stibine 3 a in a scale of 34.77 g demonstrates high synthetic potential of this transformation. The formed stibines (R3Sb) were then used for the palladium-catalyzed carbon–carbon bond forming reaction with aryl boronic acids [R−B(OH)2], giving biaryls with high selectivity, even the structures of two organomoieties (R and R′) are very similar. Plausible catalytic pathways were proposed based on control experiments.

Original languageEnglish
Pages (from-to)3104-3114
Number of pages11
JournalAngewandte Chemie - International Edition
Volume60
Issue number6
DOIs
Publication statusPublished - 8 Feb 2021

Keywords

  • biaryl synthesis
  • nickel catalysis
  • oxidative cross-coupling
  • palladium catalysis
  • Sb−C bond formation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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