74966-68-0Relevant articles and documents
Efficient synthesis of 1-iodoalkynes: Via Al2O3 mediated reaction of terminal alkynes and N -iodosuccinimide
Yao, Ming,Zhang, Jingjing,Yang, Sen,Xiong, Hangxing,Li, Li,Liu,Shi, Hong
, p. 3946 - 3950 (2020/02/04)
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.
Highly efficient recyclable sol gel polymer catalyzed one pot difunctionalization of alkynes
Domena, Justin,Chong, Carlos,Johnson, Qiaxian R.,Chauhan, Bhanu P. S.,Xing, Yalan
supporting information, (2018/08/17)
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.
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.
Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
Hokamp, Tobias,Storm, Alena Therese,Yusubov, Mekhman,Wirth, Thomas
supporting information, p. 415 - 418 (2017/10/30)
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.
Ultrasound-assisted tandem reaction of alkynes and trihaloisocyanuric acids by thiourea as catalyst in water
Zhang, Xingyu,Wu, Yundong,Zhang, Ya,Liu, Huilan,Xie, Ziyu,Fu, Shengmin,Liu, Fang
, p. 4513 - 4518 (2017/07/10)
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
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
Wu, Chao,Xin, Xiu,Fu, Zhi-Min,Xie, Long-Yong,Liu, Kai-Jian,Wang, Zheng,Li, Wenyi,Yuan, Zhi-Hui,He, Wei-Min
, p. 1983 - 1989 (2017/06/09)
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.
Iron(III) catalyzed halo-functionalization of alkynes
Catano, Bryant,Lee, John,Kim, Claudia,Farrell, David,Petersen, Jeffrey L.,Xing, Yalan
, p. 4124 - 4127 (2015/08/03)
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.
A new and efficient method for the synthesis of α,α- dihaloketones by oxyhalogenation of alkynes using oxone-KX (X = Cl, Br, or I)
Madabhushi, Sridhar,Jillella, Raveendra,Mallu, Kishore Kumar Reddy,Godala, Kondal Reddy,Vangipuram, Venkata Sairam
supporting information, p. 3993 - 3996 (2013/07/25)
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.
Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
, p. 74 - 96 (2013/04/10)
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.
Oxidative homologation of aldehydes to α-ketoaldehydes by using iodoform, o-iodoxybenzoic acid, and dimethyl sulfoxide
Zall, Andrea,Bensinger, Dennis,Schmidt, Boris
experimental part, p. 1439 - 1447 (2012/04/04)
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
