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Nickel‐ and Palladium‐Catalyzed Cross‐Coupling Reactions of Organostibines with Organoboronic Acids
Author(s) -
Zhang Dejiang,
Le Liyuan,
Qiu Renhua,
Wong WaiYeung,
Kambe Nobuaki
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202011491
Subject(s) - palladium , chemistry , alkyne , catalysis , aryl , alkene , aldehyde , nickel , combinatorial chemistry , substrate (aquarium) , coupling reaction , boronic acid , organic chemistry , alkyl , oceanography , geology
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 (R 3 Sb) 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.