13466-98-3Relevant academic research and scientific papers
Synthesis and Structure of Hypervalent Iodine(III) Reagents Containing Phthalimidate and Application to Oxidative Amination Reactions
Kiyokawa, Kensuke,Kosaka, Tomoki,Kojima, Takumi,Minakata, Satoshi
, p. 13719 - 13723 (2015)
A new class of hypervalent iodine reagents containing phthalimidate was synthesized, and structurally characterized by X-ray analysis. The benziodoxole-based reagent displays satisfactory solubility in common organic solvents and is reasonably stable in solution as well as in the solid state. The reagent was used for the oxidative amination of the C(sp3)-H bond of N,N-dimethylanilines. In addition, the reagent was also applicable to oxidative amination with rearrangement of trialkylamines as well as enamines that were prepared in situ from secondary amines and aldehydes.
Electrochemical Generation of Hypervalent Bromine(III) Compounds
Francke, Robert,Mohebbati, Nayereh,Sokolovs, Igors,Suna, Edgars
supporting information, p. 15832 - 15837 (2021/06/14)
In sharp contrast to hypervalent iodine(III) compounds, the isoelectronic bromine(III) counterparts have been little studied to date. This knowledge gap is mainly attributed to the difficult-to-control reactivity of λ3-bromanes as well as to their challenging preparation from the highly toxic and corrosive BrF3 precursor. In this context, we present a straightforward and scalable approach to chelation-stabilized λ3-bromanes by anodic oxidation of parent aryl bromides possessing two coordinating hexafluoro-2-hydroxypropanyl substituents. A series of para-substituted λ3-bromanes with remarkably high redox potentials spanning a range from 1.86 V to 2.60 V vs. Ag/AgNO3 was synthesized by the electrochemical method. We demonstrate that the intrinsic reactivity of the bench-stable bromine(III) species can be unlocked by addition of a Lewis or a Br?nsted acid. The synthetic utility of the λ3-bromane activation is exemplified by oxidative C?C, C?N, and C?O bond forming reactions.
KI-catalyzed imidation of sp3 C-H bond adjacent to amide nitrogen atom
Lao, Zhi-Qi,Zhong, Wen-He,Lou, Qing-Hua,Li, Zhong-Jun,Meng, Xiang-Bao
supporting information, p. 7869 - 7871 (2013/07/05)
We have developed a new KI-catalyzed method for the imidation of an sp 3 C-H bond adjacent to an amide nitrogen atom by using TBHP (tert-butyl hydroperoxide, 70% aqueous solution) as the oxidant. This novel procedure tolerated air and moisture and provided a series of novel products in moderate to excellent yields under mild conditions.
Photochemical Cyclisation of Phthalimide Mannich Bases
Coyle, John D.,Newport, Graham L.
, p. 93 - 96 (2007/10/02)
Ultraviolet irradiation of Mannich bases derived from phthalimide, formaldehyde, and a secondary amine leads to cyclised products containing a new imidazolidine ring.The reaction is much less efficient when the secondary amine has an aromatic group adjacent to the nitrogen atom.Exceptionally, the Mannich base derived from 3-pyrroline does not cyclise but undergoes an internal oxidation-reduction reaction to give a substituted pyrrole.
