- Decarboxylative C-H alkylation of heteroarene N-oxides by visible light/copper catalysis
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This paper reports a highly site-selective alkylation of heteroarene N-oxides using hypervalent iodine(III) carboxylates to serve as an alkylating agent in the presence of a cheap copper catalyst under visible light conditions. This mild method proceeds at room temperature in an air atmosphere and can withstand various heteroarene N-oxides as well as various primary, secondary, and tertiary alkyl carboxylic acids. It also provides a practical method for enabling the rapid conversion of commercially available raw materials into medically relevant “drug-like” molecules.
- Liu, Duan-Yang,Liu, Xu,Gao, Yan,Wang, Chao-Qun,Tian, Jie-Sheng,Loh, Teck-Peng
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supporting information
p. 8978 - 8983
(2020/11/30)
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- Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate
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A practical method for the preparation of (diacetoxyiodo)arene ArI(OAc)2 is described. The use of commercially available sodium hypochlorite pentahydrate (NaClO·5H2O) enabled safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing and -donating substituents. The method allows tandem divergent access to synthetically useful organo-λ3-iodanes such as hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.
- Watanabe, Ayumi,Miyamoto, Kazunori,Okada, Tomohide,Asawa, Tomotake,Uchiyama, Masanobu
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p. 14262 - 14268
(2018/11/23)
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- N -Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts to Generate α,β-Unsaturated Ketones
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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.
- Rajkiewicz, Adam A.,Kalek, Marcin
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supporting information
p. 1906 - 1909
(2018/04/16)
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- Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
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A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).
- Zhao, Chun-Yang,Li, Kun,Pang, Yu,Li, Jia-Qing,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
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supporting information
p. 1919 - 1925
(2018/03/28)
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- Alternative Strategies with Iodine: Fast Access to Previously Inaccessible Iodine(III) Compounds
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Non-iodinated arenes can be easily and selectively converted into (diacetoxyiodo)arenes in a single step under mild conditions by using iodine triacetates as reagents. The oxidative step is decoupled from the synthesis of hypervalent iodine(III) reagents, which can now be prepared conveniently in a one-pot synthesis for subsequent reactions without prior purification. The chemistry of iodine triacetates was also expanded to heteroatom ligand exchanges to form novel inorganic hypervalent iodine compounds.
- Hokamp, Tobias,Mollari, Leonardo,Wilkins, Lewis C.,Melen, Rebecca L.,Wirth, Thomas
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supporting information
p. 8306 - 8309
(2018/06/29)
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- Synthesis of O -Aroyl- N, N -dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N, N -Dimethylformamide
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An efficient protocol for the synthesis of O -aroyl- N, N -dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N, N -dimethylformamide is mediated by hypervalent iodine and
- Zhang, Chuancheng,Yue, Qiang,Xiao, Zhen,Wang, Xianglan,Zhang, Qian,Li, Dong
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supporting information
p. 4303 - 4308
(2017/09/13)
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- Room-Temperature Gold-Catalysed Arylation of Heteroarenes: Complementarity to Palladium Catalysis
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Tailoring of the pre-catalyst, the oxidant and the arylsilane enables the first room-temperature, gold-catalysed, innate C?H arylation of heteroarenes. Regioselectivity is consistently high and, in some cases, distinct from that reported with palladium ca
- Cresswell, Alexander J.,Lloyd-Jones, Guy C.
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supporting information
p. 12641 - 12645
(2016/08/30)
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- NH-Heterocyclic Aryliodonium Salts and their Selective Conversion into N1-Aryl-5-iodoimidazoles
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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.
- Wu, Yichen,Izquierdo, Susana,Vidossich, Pietro,Lledós, Agustí,Shafir, Alexandr
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supporting information
p. 7152 - 7156
(2016/07/06)
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- Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives
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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.
- Holt, Dean,Gaunt, Matthew J.
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supporting information
p. 7857 - 7861
(2015/06/30)
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- Synthesis and reactivity of aryl(alkynyl)iodonium salts
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The first practical, yet simple, preparation of aryl(alkynyl)iodonium trifluoroacetate salts is described. The generic nature of this synthetic method has allowed the production of a range of aryl(alkynyl)iodonium trifluoroacetate salts with independent variation of both the alkynyl and aryliodo groups in yields of 30-85 %. Application of these new reagents to the synthesis of a series of 2-arylfuro[3,2-c]pyridines (40-64 %) highlights the potential of this class of materials as precursors to bioactive heterocyclic structures. These experiments have also demonstrated that, in this case, the effect of the aryliodo group on the reaction is negligible.
- Dixon, Luke I.,Carroll, Michael A.,Gregson, Thomas J.,Ellames, George J.,Harrington, Ross W.,Clegg, William
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supporting information
p. 2334 - 2345
(2013/05/21)
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- NAPHTHALENE DERIVATIVE
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The present invention provides compounds which can regulate VCP activity. The present invention provides the compound of formula (I) (R is as defined in the description) or oxides, esters, prodrugs, pharmaceutically acceptable salts or solvates thereof. The compounds can regulate VCP activity, and thus are useful for treating VCP-mediated diseases such as neurodegenerative diseases.
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Paragraph 0437
(2013/06/27)
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- AGENT FOR TREATMENT OF EYE DISEASES
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The present invention provides agents effective to treat eye diseases, pharmaceutical compositions comprising them, methods for preparing pharmaceuticals for treatment of eye diseases comprising using the agents, use of the agents in manufacture of pharma
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Paragraph 0270-0271
(2013/08/15)
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- Straightforward syntheses of hypervalent iodine(III) reagents mediated by selectfluor
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(Chemical Equation Presented) Use of Selectfluor allows hypervalent iodine(III) species such as aryl iodine(III) difluoride, diacetate, and di(trifluoroacetate) and Koser's salt to be easily prepared. Aryl iodine(III) difluoride and diacetate can be synthesized from the corresponding arene and elemental iodine in one-pot procedures.
- Ye, Chengfeng,Twamley, Brendan,Shreeve, Jean'ne M.
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p. 3961 - 3964
(2007/10/03)
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- Synthesis of 3-aryloxy-2-iodoemodines by oxidation of emodin with (diacetoxyiodo)arenes
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Hypervalent iodine oxidation of emodin (1) with various (diacetoxyiodo)arenes 2a-f in potassium hydroxide/methanol leading to 3-aryloxy-1,8-dihydroxy-2-iodo-anthraquinones 4a-f is reported. Mechanistic studies showed reaction via iodonium ylides. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Daub, Katja S.,Habermann, Bernd,Hahn, Thilo,Teich, Lars,Eger, Kurt
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p. 894 - 898
(2007/10/03)
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- Synthesis of functionalised unsymmetrical diaryliodonium salts
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A generalised synthesis of unsymmetrical functionalised diaryliodonium salts has been developed through the direct reaction of bis(acetoxy)iodoarenes with arenes in a trifluoromethanesulfonic or trifluoroacetic acid medium.
- Shah, Aneela,Pike, Victor W.,Widdowson, David A.
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p. 2463 - 2465
(2007/10/03)
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