623-12-1Relevant articles and documents
Shamma et al.
, p. 3335 (1968)
Chlorination and bromination of aromatic molecules by an N-halosaccharin/pyridinium poly(hydrogen fluoride) system
Mozek,Sket
, p. 2513 - 2520 (1992)
The title chlorination and bromination procedure can be used for ring halogenation of monosubstituted benzene derivatives. Reactions do not need the addition of any catalyst and take place under mild conditions.
Matsue et al.
, p. 3692,3693, 3694 (1979)
PhICl2is activated by chloride ions
Tania,Poynder, Tiffany B.,Kaur, Aishvaryadeep,Barwise, Lachlan,Houston, Sevan D.,Nair, Akshay J.,Clegg, Jack K.,Wilson, David J. D.,Dutton, Jason L.
supporting information, p. 11986 - 11991 (2021/09/06)
A study on the potential activating role of pyridine in the electrophilic chlorination of anisole by PhICl2has led to the discovery that soluble sources of chloride ions activate PhICl2in the reaction at catalytic loadings, greatly increasing the rate of chlorination. It is further shown that presence of chloride increases the rate of decomposition of PhICl2into PhI and Cl2. The specific mechanism by which chloride induces electrophilic chlorination and decomposition of PhICl2remains an open question.
R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond
Bondarenko, Oksana B.,Karetnikov, Georgy L.,Komarov, Arseniy I.,Pavlov, Aleksandr I.,Nikolaeva, Svetlana N.
supporting information, p. 322 - 332 (2021/01/14)
A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.
Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
supporting information, p. 20543 - 20550 (2021/08/12)
Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
