@article{1e723a455ec7418fb235ab6076e67a3d,
title = "Nickel- and Palladium-Catalyzed Cross-Coupling Reactions of Organostibines with Organoboronic Acids",
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.",
keywords = "biaryl synthesis, nickel catalysis, oxidative cross-coupling, palladium catalysis, Sb−C bond formation",
author = "Dejiang Zhang and Liyuan Le and Renhua Qiu and Wong, {Wai Yeung} and Nobuaki Kambe",
note = "Funding Information: This research was supported by the National Natural Science Foundation of China (21676076, 21878071, 21971060), Recruitment Program of China (WQ20164300353), and Hu-Xiang High-Talent Project of Hunan Province (2018RS3042). R.Q. thanks Prof. S.-F. Yin (Hunan University), Prof. Dr. T. Iwasaki (The University of Tokyo), Prof. C.-T. Au (Hong Kong Baptist University) for helpful discussions. W.-Y.W. thanks the Hong Kong Polytechnic University (1-ZE1C) and Ms Clarea Au for the Endowed Professorship in Energy (847S). Funding Information: This research was supported by the National Natural Science Foundation of China (21676076, 21878071, 21971060), Recruitment Program of China (WQ20164300353), and Hu‐Xiang High‐Talent Project of Hunan Province (2018RS3042). R.Q. thanks Prof. S.‐F. Yin (Hunan University), Prof. Dr. T. Iwasaki (The University of Tokyo), Prof. C.‐T. Au (Hong Kong Baptist University) for helpful discussions. W.‐Y.W. thanks the Hong Kong Polytechnic University (1‐ZE1C) and Ms Clarea Au for the Endowed Professorship in Energy (847S). Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",
year = "2021",
month = feb,
day = "8",
doi = "10.1002/anie.202011491",
language = "English",
volume = "60",
pages = "3104--3114",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "6",
}