31599-59-4Relevant academic research and scientific papers
Conformational structure and energetics of 2- methylphenyl(2′methoxyphenyl)iodonium chloride: Evidence for solution clusters
Lee, Yong-Sok,Hodoscek, Milan,Chun, Joong-Hyun,Pike, Victor W.
, p. 10418 - 10423 (2010)
Diaryliodonium salts allow the efficient incorporation of cyclotronproduced [18F]fluoride ions into electron-rich and electron-deficient arenes to provide potential radiotracers for molecular imaging in vivo with positron emission tomography (P
Cu-catalyzed [2 + 2 + 1] cascade annulation of vinyl iodonium salts with elemental sulfur/selenium for the modular synthesis of thiophenes and selenophenes
Chen, Chao,Wang, Fei,Wu, Chao,Wu, Yaxing
, p. 945 - 949 (2022/02/01)
A [2 + 2 + 1] annulation protocol has been established for the modular synthesis of 2,4-disubstituted thiophenes/selenophenes, with excellent regioselectivity. The reactions have been catalyzed by copper salt with elemental sulfur and selenium serving as
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 (2021/04/22)
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.
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.
N -Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts to Generate α,β-Unsaturated Ketones
Rajkiewicz, Adam A.,Kalek, Marcin
supporting information, p. 1906 - 1909 (2018/04/16)
An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.
Heterocyclic ring aromatic ether compound and synthesis method thereof
-
Paragraph 0038; 0039; 0040, (2017/07/19)
The invention discloses a heterocyclic ring aromatic ether compound and a synthesis method thereof, and belongs to the technical field of organic synthesis. The heterocyclic ring aromatic ether compound is mainly characterized in that the heterocyclic ring aromatic ether compound has the following structure general formula shown as the accompanying drawing, wherein R1 and R2 are correspondingly and respectively shown as follows: (1) R1 H, and R2 is H; (2) R1 is H, and R2 is Me; (3) R1 is Me, and R2 H. The invention concretely discloses the synthesis method of the heterocyclic ring aromatic ether compound. A mixed solution of acetic anhydride and acetic acid is used for replacing peroxyacetic acid or trifluoromethanesulfonic acid with high corrosiveness; the operation is safer and easier; the industrial production is facilitated; in addition, the heterocyclic ring aromatic ether compound is obtained through oxidizing 4-pyridone by iodonium oxidizing agents.
Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols to Form Allylic Quaternary Centers
Patel, Harshkumar H.,Sigman, Matthew S.
supporting information, p. 14226 - 14229 (2016/11/13)
In this report, we describe the generation of remote allylic quaternary stereocenters β, γ, and δ relative to a carbonyl in high enantioselectivity. We utilize a redox-relay Heck reaction between alkenyl triflates and acyclic trisubstituted alkenols of varying chain-lengths. A wide array of terminal (E)-alkenyl triflates are suitable for this process. The utility of this functionalization is validated further by conversion of the products, via simple organic processes to access remotely functionalized chiral tertiary acid, amine, and alcohol products.
An Investigation of (Diacetoxyiodo)arenes as Precursors for Preparing No-Carrier-Added [18F]Fluoroarenes from Cyclotron-Produced [18F]Fluoride Ion
Haskali, Mohammad B.,Telu, Sanjay,Lee, Yong-Sok,Morse, Cheryl L.,Lu, Shuiyu,Pike, Victor W.
, p. 297 - 302 (2016/01/15)
Treatment of (diacetoxyiodo)arenes (1a-1u) with cyclotron-produced [18F]fluoride ion rapidly affords no-carrier-added [18F]fluoroarenes (2a-2u) in useful yields and constitutes a new method for converting substituted iodoarenes into substituted [18F]fluoroarenes in just two steps.
NH-Heterocyclic Aryliodonium Salts and their Selective Conversion into N1-Aryl-5-iodoimidazoles
Wu, Yichen,Izquierdo, Susana,Vidossich, Pietro,Lledós, Agustí,Shafir, Alexandr
supporting information, p. 7152 - 7156 (2016/07/06)
The synthesis of N-arylimidazoles substituted at the sterically encumbered 5-position is a challenge for modern synthetic approaches. A new family of imidazolyl aryliodonium salts is reported, which serve as a stepping stone on the way to selective formation of N1-aryl-5-iodoimidazoles. Iodine acts as a “universal” placeholder poised for replacement by aryl substituents. These new λ3-iodanes are produced by treating the NH-imidazole with ArI(OAc)2, and are converted to N1-aryl-5-iodoimidazoles by a selective copper-catalyzed aryl migration. The method tolerates a variety of aryl fragments and is also applicable to substituted imidazoles.
Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives
Holt, Dean,Gaunt, Matthew J.
supporting information, p. 7857 - 7861 (2015/06/30)
A novel method for the synthesis of a wide range of functionalized 1,3-diol derivatives is reported. Employing a copper-catalyzed oxy-alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn-1,3-carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments. Polyols: The reported copper-catalyzed oxy-alkenylation strategy works well for a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts to form syn-1,3-carbonates in excellent yield and high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments.
