Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes

Dejiang Zhang, Ting Tang, Zhao Zhang, Liyuan Le, Zhi Xu, Hao Lu, Zhou Tong, Dishu Zeng, Wai Yeung Wong, Shuang Feng Yin, Arash Ghaderi, Nobuaki Kambe, Renhua Qiu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

4 Citations (Scopus)

Abstract

Herein, we disclose a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines by the nickel-catalyzed cross-coupling of halostibines with organic halides. The synthesized Sb-aryl stibines couple with aryl halides to give biaryls efficiently via palladium catalysis. Sequential reactions of stibines with polyhalogenated arenes bearing active C–I/C–Br sites and inactive C–Cl sites successfully proceeded, resulting in the formation of a variety of complex molecules with good site selectivity. Drugs such as diflunisal and fenbufen, as well as a fenofibrate derivative, were synthesized on gram scales in good yields, together with the high recovery of chlorostibine. Furthermore, catalytic mechanisms are proposed based on the results of control experiments.

Original languageEnglish
Pages (from-to)854-867
Number of pages14
JournalACS Catalysis
Volume12
Issue number2
Early online date29 Dec 2021
DOIs
Publication statusPublished - Jan 2022

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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