28896-47-1Relevant articles and documents
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Deacon et al.
, p. 111,118 (1978)
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Fluorocyclization of N-Propargyl Carboxamides by λ3-Iodane Catalysts with Coordinating Substituents
Takahashi, Shunsuke,Umakoshi, Yuki,Nakayama, Kaii,Okada, Yohei,Zhdankin, Viktor V.,Yoshimura, Akira,Saito, Akio
supporting information, p. 2997 - 3003 (2020/06/17)
Aiming at the enhanced catalytic activity of fluoro-λ3-iodane generated from iodoarene precatalyst with Selectfluor and HF?pyridine, this study focused on the λ3-iodanes bearing coordinating substituents. Compared to 4-iodoanisole as a precatalyst of our previous method, N-methyl-2-iodobenzamide or 2-iodobenzamide worked well in the fluorocyclization of N-propargyl carboxamides to oxazoles. Control experiments suggest the equilibrium mixture of iodane-amine complexes and cyclic iodane fluorides would be involved in the present catalysis. (Figure presented.).
Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones
Zhang, Jingyu,Li, Shiguang,Deng, Guo-Jun,Gong, Hang
, p. 376 - 380 (2017/12/07)
A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chemistry and provides an avenue for the convenient direct iodination of arenes and ketones.
Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
Perry, Gregory J. P.,Quibell, Jacob M.,Panigrahi, Adyasha,Larrosa, Igor
, p. 11527 - 11536 (2017/08/30)
Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.