4.8 Article

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

Journal

ACS CATALYSIS
Volume 12, Issue 2, Pages 854-867

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c04533

Keywords

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

Funding

  1. National Natural Science Foundation of China [21676076, 21878071, 21971060]
  2. Recruitment Program for Foreign Experts of China [WQ20164300353]
  3. Hu-Xiang High-Talent Project of Hunan Province [2018RS3042]
  4. Hong Kong Polytechnic University [1-ZE1C]
  5. Ms Clarea Au for the Endowed Professorship in Energy [847S]
  6. Hong Kong Research Grant Council [PolyU 15305320]

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This study presents a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines through nickel-catalyzed cross-coupling reactions with organic halides. The method enables the high selectivity synthesis of complex biaryls and successfully synthesized various molecules, including drugs, with good yields.
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.

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