904689-24-3Relevant academic research and scientific papers
Nickel- and Palladium-Catalyzed Cross-Coupling Reactions of Organostibines with Organoboronic Acids
Zhang, Dejiang,Le, Liyuan,Qiu, Renhua,Wong, Wai-Yeung,Kambe, Nobuaki
supporting information, p. 3104 - 3114 (2020/12/11)
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.
Stimuli-Responsive B/N Lewis Pairs Based on the Modulation of B-N Bond Strength
Hou, Qinggao,Liu, Lijie,Mellerup, Soren K.,Wang, Nan,Peng, Tai,Chen, Pangkuan,Wang, Suning
, p. 6467 - 6470 (2018/10/15)
A series of robust organoboranes with electronically tunable functionality of B/N Lewis pairs has been achieved. These compounds feature a B/N-containing core in which the interactions between the B and N atoms are modulated as a result of the structural
An expeditious N,N-dibenzylation of anilines under ultrasonic irradiation conditions using low loading Cu(II)-clay heterogeneous catalyst
Dar, Bashir Ahmad,Shrivastava, Varsha,Bowmik, Amrita,Wagay, Mohammad Arif,Singh, Baldev
, p. 136 - 141 (2015/02/02)
A simple one-pot procedure for the direct N,N-dibenzylation of anilines using a catalytic amount of Cu modified montmorillonite-KSF is described. Cu modified montmorillonite-KSF has been proven to be a simple, efficient, mild, convenient, and effective catalyst for the selective benzylation of anilines with benzyl bromide. Cu loading plays a significant role in product yield and solvents were found to control the selectivity. The catalyst is easy to prepare, heterogeneous, stable, and easy to recover.
Hypervalent organoantimony compounds 12-ethynyl-tetrahydrodibenz[c,f][1,5]azastibocines: Highly efficient new transmetallating agent for organic halides
Kakusawa, Naoki,Tobiyasu, Yoshinori,Yasuike, Shuji,Yamaguchi, Kentaro,Seki, Hiroko,Kurita, Jyoji
, p. 2953 - 2968 (2007/10/03)
Extremely efficient and high-speed ethynylation of acyl chlorides, aryl iodides and bromides was demonstrated by palladium-catalyzed cross-coupling reaction of N-t-butyl-Sb-ethynyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine under mild conditions. Optimization and generalization of the hypervalent antimony-mediated coupling reaction are presented in detail. Single-crystal X-ray analysis of the N-methyl-1,5-azastibocine revealed that the remarkable reactivity enhancement of the azastibocine was derived from elongation of the antimony-ethynyl carbon bond originated from Sb-N intramolecular non-bonding interaction.
