42984-87-2Relevant academic research and scientific papers
Desulfurization of dibenzothiophene and dibenzothiophene sulfone via Suzuki–Miyaura type reaction: Direct access to o-terphenyls and polyphenyl derivatives
Gutiérrez-Ordaz, Rubén,García, Juventino J.
, p. 373 - 381 (2018/08/31)
The reactivity of dibenzothiophene (DBT) or dibenzothiophene sulfone (DBTO2) with a variety of phenylboronic acids was mediated by the nickel precursor [Ni(dippe)Cl2] in the presence of a base. The reaction was performed under relatively mild conditions (70–100 °C), in aqueous media. The study of the reactivity revealed the role of water as a hydrogen source and showed a competition between the desulfurization of the corresponding substrates via a hydrodesulfurization (HDS) or by a hydrodesulfurative cross-coupling (HDSCC) reaction. Furthermore, in the absence of water sulfur-free poly-phenylic compounds were obtained in good yields as a result of a Suzuki–Miyaura type reaction, being the main product in most of the cases the corresponding o-terphenyl derivative, these products are valuable building blocks in the synthesis of more complex materials.
Cross-coupling Reaction of Aryl Grignard Reagents with Aromatic Halides catakyzed by Bis(acetylacetonato)nickel(II)
Ibuki, Eiichi,Ozasa, Shigeru,Fujioka, Yasuhiro,Yanagihara, Yoshihiko
, p. 802 - 809 (2007/10/02)
A series of cross-coupling reactions of aryl Grignard reagents with aromatic iodides catalyzed by bis(acetylacetonato)nickel(II) was studied to establish reaction conditions under which the cross-coupling proceeded selectively and quantitatively.Under the standard conditions thus selected, the coupling reactions proceeded within a few hours by a simple procedure and gave very pure product in high yield.Thus, the Kharash-type cross-coupling reaction was found to be very useful for the synthesis of a variety of polyphenyls.With some reactants of more or less crowded geometry, the reaction resulted in rather low yields of polyphenyls.This cross-coupling was successfully applied to the synthesis of a new compound, 2,6,2',6'-tetraphenylbiphenyl, having a highly non-planar arrangement of ?-systems.
