16308-16-0Relevant academic research and scientific papers
Applications of hypervalent iodine(III) reagents in constructing ortho-iodo aromatic ethers
Bao-Hua, Hou,De-Jun, Zhou,Ke-Yang, Wang,Peng-Wei, Liu,Xiao-Rui, Cui,Xue-Yan, Li,Xue-Yun, Gong,Yan-Feng, Sun,Yang-Yang, Zhai,Zhen-Hui, Wang
, p. 818 - 822 (2021)
A one-pot method for the synthesis of aromatic ethers using hypervalent iodine(III) reagents obtained from the corresponding iodoaryl compounds is developed. In this concise method, six diaryl ethers and three heterocyclic aromatic ethers are synthesized in good yields. Furthermore, possible mechanisms for the syntheses of the hypervalent iodine reagents and construction of the aromatic ethers are proposed.
Organoiodine-catalyzed oxidative spirocyclization of phenols using peracetic acid as a green and economic terminal oxidant
Minamitsuji, Yutaka,Kato, Daishi,Fujioka, Hiromichi,Dohi, Toshifumi,Kita, Yasuyuki
, p. 648 - 652 (2009)
The use of peracetic acid as a green and economical terminal oxidant in fluoroalcohol solvents could provide a practical iodoarene-catalyzed oxidation of phenols to give spirodienones. Acetic acid and water were the only co-products and waste, and thus th
Photocatalytic Fluoro Sulfoximidations of Styrenes
Bolm, Carsten,Ma, Ding,Tu, Yongliang,Wang, Chenyang
, p. 14134 - 14137 (2020)
Reactions of difluoroiodotoluene with NH-sulfoximines provide new hypervalent iodine(III) reagents, which photocatalytically transfer a fluoro and a sulfoximidoyl group onto styrenes with high regioselectivity. The substrate scope is broad with respect to
Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts
Antonkin, Nikita S.,Vlasenko, Yulia A.,Yoshimura, Akira,Smirnov, Vladimir I.,Borodina, Tatyana N.,Zhdankin, Viktor V.,Yusubov, Mekhman S.,Shafir, Alexandr,Postnikov, Pavel S.
, p. 7163 - 7178 (2021/05/29)
A novel approach to the preparation of imidazole-substituted cyclic iodonium salts has been developed via the oxidative cyclization of 1-phenyl-5-iodoimidazole using a cheap and available Oxone/H2SO4 oxidative system. The structure of the new polycyclic heteroarenes has been confirmed by single-crystal X-ray diffractometry, revealing the characteristic structure features for cyclic iodonium salts. The newly produced imidazole-flanked cyclic iodonium compounds were found to readily engage in a heterocyclization reaction with elemental sulfur, affording benzo[5,1-b]imidazothiazoles in good yields.
Method for producing hypervalent iodine compound
-
Paragraph 0065-0066, (2020/12/31)
The invention provides a method for producing a hypervalent iodine compound; the method is more effective than the prior art, improves yield while reducing reaction time, and is more suitable for industrial application.
The Role of Iodanyl Radicals as Critical Chain Carriers in Aerobic Hypervalent Iodine Chemistry
Hyun, Sung-Min,Yuan, Mingbin,Maity, Asim,Gutierrez, Osvaldo,Powers, David C.
supporting information, p. 2388 - 2404 (2019/09/12)
Selective O2 utilization remains a substantial challenge in synthetic chemistry. Biological small-molecule oxidation reactions often utilize aerobically generated high-valent catalyst intermediates to effect substrate oxidation. Available synthetic methods for aerobic oxidation catalysis are largely limited to substrate functionalization chemistry by low-valent catalyst intermediates (i.e., aerobically generated Pd(II) intermediates). Motivated by the need for new chemical platforms for aerobic oxidation catalysis, we recently developed aerobic hypervalent iodine chemistry. Here, we report that in contrast to the canonical two-electron oxidation mechanisms for the oxidation of organoiodides, the developed aerobic hypervalent iodine chemistry proceeds via a radical chain mechanism initiated by the addition of aerobically generated acetoxy radicals to aryl iodides. Despite the radical chain mechanism, aerobic hypervalent iodine chemistry displays substrate tolerance similar to that observed with traditional terminal oxidants, such as peracids. We anticipate that these insights will enable new sustainable oxidation chemistry via hypervalent iodine intermediates. O2 is routinely utilized in biological catalysis to generate high-valent catalyst intermediates that engage in substrate oxidation chemistry. Analogous synthetic chemistry via aerobically generated high-valent intermediates would enable new sustainable synthetic methods but is largely unknown because of the challenges in selective O2 utilization. We have developed aerobic hypervalent iodine chemistry as a platform for coupling O2 reduction with a diverse set of substrate functionalization mechanisms. Many of the synthetic applications of hypervalent iodine reagents rely on selective two-electron oxidation-reduction chemistry. Here, we report that one-electron oxidation reactions pathways via iodanyl radical intermediates are critical in aerobic hypervalent iodine chemistry. The new appreciation for the critical role that iodanyl radicals can play in the synthesis of hypervalent iodine compounds will provide new opportunities in sustainable oxidation catalysis. Aerobic hypervalent iodine chemistry provides a strategy for coupling the one-electron chemistry of O2 with two-electron processes typical of organic synthesis. We show that in contrast to the canonical two-electron oxidation of aryl iodides, aerobic synthesis proceeds by a radical chain process initiated by the addition of aerobically generated acetoxy radicals to aryliodides to generate iodanyl radicals. Robustness analysis reveals that the developed aerobic oxidation chemistry displays substrate tolerance similar to that observed in peracid-based methods and thus holds promise as a sustainable synthetic method.
SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN
-
Paragraph 0071-0072, (2019/01/15)
Methods of synthesis of hypervalent iodine reagents and methods for oxidation of organic compounds are disclosed.
Iodosylbenzene Coordination Chemistry Relevant to Metal-Organic Framework Catalysis
Cardenal, Ashley D.,Maity, Asim,Gao, Wen-Yang,Ashirov, Rahym,Hyun, Sung-Min,Powers, David C.
supporting information, p. 10543 - 10553 (2019/09/13)
Hypervalent iodine compounds formally feature expanded valence shells at iodine. These reagents are broadly used in synthetic chemistry due to the ability to participate in well-defined oxidation-reduction processes and because the ligand-exchange chemist
A trivalent hypervalent iodine compound using hypochlorite (by machine translation)
-
Paragraph 0066, (2020/02/14)
[A] used in the prior art organic salt, toxic chlorine gas, organic peroxides can be used without the novel trivalent hypervalent iodine compound production. Furthermore, the acyloxy groups other than the trivalent hypervalent iodine compounds having a ligand manufacturing method. (1) Formula [solution](In the formula, R1 Substituted/unsubstituted aromatic group, aliphatic group or the like. N is an integer of 1 or more. ) Represented by the iodine compound, carboxylic acid, carboxylic acid anhydride, a sulfonic acid or sulfonic acid anhydride with at least one organic acid selected from the group consisting of, a hypochlorite mixing, trivalent hypervalent iodine compound. [Drawing] no (by machine translation)
Preparation method of p-methyl iodobenzene diacetate
-
Paragraph 0011; 0012; 0013; 0014, (2018/05/16)
The invention relates to a preparation method of p-methyl iodobenzene diacetate. P-methyl iodobenzene and glacial acetic acid are added to a round-bottom flask, acetic anhydride is added after dissolution, the round-bottom flask is placed in an oil bath pan at 50 DEG C for magnetic stirring, NaBO3.4H2O is added, and the mixture is heated to react for 24 h. After the reaction ends, the product is left to stand, taken out and cooled to the room temperature, distilled water is added, suction filtration is performed, washing and extraction are performed with DCM 3 times, filtrate is collected, organic phases are mixed, drying is performed with anhydrous Na2SO4, filtration is performed, a solvent is removed, diethyl ether is added for cooling crystallization, white crystals separate out, suction filtration and drying are performed, and an iodobenzene diacetate derivative is obtained. The method adopts mild reaction conditions, has high selectivity, has the yield of 92% and is environmentally friendly.
