- Efficient synthesis of 1-iodoalkynes: Via Al2O3 mediated reaction of terminal alkynes and N -iodosuccinimide
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Iodination of terminal alkynes using N-iodosuccinimide (NIS) in the presence of γ-Al2O3 was developed to afford 1-iodoalkynes with good to excellent yields (up to 99%). This described approach featured excellent chemoselectivity, good functional group tolerance, and utilization of an inexpensive catalyst.
- Yao, Ming,Zhang, Jingjing,Yang, Sen,Xiong, Hangxing,Li, Li,Liu,Shi, Hong
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p. 3946 - 3950
(2020/02/04)
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- Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones
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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.
- Zhang, Jingyu,Li, Shiguang,Deng, Guo-Jun,Gong, Hang
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p. 376 - 380
(2017/12/07)
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- Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
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A novel and inexpensive, environmentally friendly method for the preparation of iodine monoacetate is presented using iodine and Oxone in acetic acid/acetic anhydride. The reagent is used in a highly efficient approach for the regio- and diastereoselective iodo-acetoxylation of alkenes and alkynes in a simple one-pot process.
- Hokamp, Tobias,Storm, Alena Therese,Yusubov, Mekhman,Wirth, Thomas
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supporting information
p. 415 - 418
(2017/10/30)
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- Highly efficient recyclable sol gel polymer catalyzed one pot difunctionalization of alkynes
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Amino-bridged gel polymer P1 was discovered to catalyze alkyne halo-functionalization in excellent yields, regioselectivity, functional group compatibility, and recyclability. We have observed that both aromatic and aliphatic alkynes can be converted to α,α-dihalogenated ketones in the presence of polymer P1 under metal-free conditions at room temperature within a short reaction time.
- Domena, Justin,Chong, Carlos,Johnson, Qiaxian R.,Chauhan, Bhanu P. S.,Xing, Yalan
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supporting information
(2018/08/17)
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- Ultrasound-assisted tandem reaction of alkynes and trihaloisocyanuric acids by thiourea as catalyst in water
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With water as the sole solvent, a green and efficient method has been developed for the synthesis of various α,α-dihaloketones via ultrasound assisted p-tolylthiourea catalyzed tandem reaction of alkynes with trihaloisocyanuric acids. This synthetic route
- Zhang, Xingyu,Wu, Yundong,Zhang, Ya,Liu, Huilan,Xie, Ziyu,Fu, Shengmin,Liu, Fang
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p. 4513 - 4518
(2017/07/10)
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- Water-controlled selective preparation of α-mono or α,α′-dihalo ketones: Via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin
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The control of a reaction that can produce multiple products from the same starting material is a highly attractive and challenging concept in organic synthesis. An efficient protocol for the selective synthesis of α-mono or α,α′-dihalo ketones via a water-controlled three-component thiourea-catalyzed cascade reaction of unactivated alkynes, 1,3-dihalo-5,5-dimethylhydantoin and water has been developed. α-Monohaloketones were obtained in aqueous acetone at 45 °C; conversely, α,α′-dihalo ketones were formed with pure water as the sole solvent at room temperature.
- Wu, Chao,Xin, Xiu,Fu, Zhi-Min,Xie, Long-Yong,Liu, Kai-Jian,Wang, Zheng,Li, Wenyi,Yuan, Zhi-Hui,He, Wei-Min
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p. 1983 - 1989
(2017/06/09)
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- Iron(III) catalyzed halo-functionalization of alkynes
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Abstract Aromatic and aliphatic alkynes can be halo-functionalized to α,α-dihalodimethyl ketals catalyzed by FeCl3 in excellent yields. MeOH is used as a nucleophilic solvent and N-halosuccinimide as the halogen source for this efficient transformation. The resulting α,α-dibromodimethyl ketals can be converted to the corresponding α,α-dibromoketones by treatment with 8% FeCl3 in silica gel.
- Catano, Bryant,Lee, John,Kim, Claudia,Farrell, David,Petersen, Jeffrey L.,Xing, Yalan
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p. 4124 - 4127
(2015/08/03)
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- A new and efficient method for the synthesis of α,α- dihaloketones by oxyhalogenation of alkynes using oxone-KX (X = Cl, Br, or I)
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A simple and efficient method for the preparation of α,α- dichloroketones, α,α-dibromoketones, and α,α- diiodoketones by oxyhalogenation of alkynes using oxone and KX (X = Cl, Br, or I) is described.
- Madabhushi, Sridhar,Jillella, Raveendra,Mallu, Kishore Kumar Reddy,Godala, Kondal Reddy,Vangipuram, Venkata Sairam
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supporting information
p. 3993 - 3996
(2013/07/25)
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- Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
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The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.
- Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
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- Oxidative homologation of aldehydes to α-ketoaldehydes by using iodoform, o-iodoxybenzoic acid, and dimethyl sulfoxide
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An efficient three-step synthetic route to α-ketoaldehydes starting from aryl aldehydes is reported. The aldehydes were treated with iPrMgCl and iodoform to obtain β-diiodoalcohols, which were then oxidized with o-iodoxybenzoic acid at room temperature to the corresponding β-diiodoketones. Subsequent reaction of the β-diiodoketone to the α-ketoaldehyde occurred under oxygen transfer from dimethyl sulfoxide. These sensitive products were in situ cyclized with o-phenylenediamine to form the stable monosubstituted quinoxalines, which could be characterized and isolated easily. α-Ketoaldehydes are a versatile, highly reactive moiety for the synthesis of heterocyclic compounds. We investigated the transformation of aldehydes into α-ketoaldehydes via β-diiodoketone intermediates and finally applied the procedure to the synthesis of peptidic substrates. Copyright
- Zall, Andrea,Bensinger, Dennis,Schmidt, Boris
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experimental part
p. 1439 - 1447
(2012/04/04)
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- Selective 1,2-dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides
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1,2-Dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides can be selectively realized through using different reaction conditions. α,β-Dihalo alkenes were obtained exclusively using THF as solvent without using any catalyst, while α,α
- Liu, Jinhua,Li, Wenjuan,Wang, Chao,Li, Yao,Li, Zhiping
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supporting information; experimental part
p. 4320 - 4323
(2011/09/12)
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- Reactions of Terminal Alkynes with Iodine in Methanol
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Terminal alkynes 1-hexyne (1), tert-butylacetylene (2), and phenylacetylene (3) react with iodine in methanol to give only 1,2-diiodoalkenes.If the reactions are carried out in the presence of silver nitrate, however, diiodo ketones (RC(O)CHI2) and substi
- Heasley, Victor L.,Shellhammer, Dale F.,Heasley, Lynn E.,Yaeger, David B.,Heasley, Gene E.
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p. 4649 - 4652
(2007/10/02)
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