71022-74-7Relevant academic research and scientific papers
THE FACILE SYNTHESIS OF DIIODOALKENES BY THE ADDITION OF I2 TO ALKYNES ON ALUMINA
Larson, Steven,Luidhardt, Teresa,Kabalka, George W.,Pagni, Richard M.
, p. 35 - 36 (1988)
Iodine adds to a variety of alkynes on alumina at or slightly above room temperature to form diiodoalkenes.
Stereoselective synthesis of either E- or Z-diiodoalkenes from alkynes using ICl and iodide
Henaff, Nadine,Stewart, Sarah K.,Whiting, Andrew
, p. 4525 - 4526 (1997)
Reaction of alkynes with ICl and an iodide source results in the stereoselective formation of diiodoalkenes in moderate to high yield. At r.t., the reaction is stereospecific, resulting in the formation of E-diiodoalkenes, however lowering the temperature
Facile synthesis of E-diiodoalkenes: H2O2-activated reaction of alkynes with iodine
Terent'ev, Alexander O.,Borisov, Dmitry A.,Krylov, Igor B.,Nikishin, Gennady I.
, p. 3151 - 3164 (2007)
Hydrogen peroxide was found to activate iodine in the addition reaction with triple bonds. A facile and technologically straightforward procedure was developed for the synthesis of E-diiodoalkenes based on the reaction of alkynes with an I2-H2O2 system in
Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2
Hammond, Gerald B.,Liu, Shiwen,Xu, Bo,Yang, Yi,Yang, Yuhao,Zeng, Xiaojun
supporting information, p. 1018 - 1031 (2020/04/08)
We describe a catalyst-free 1,2-trans-dihalogenation of alkynes with an unprecedented substrate scope and exclusive regio- and stereoselectivity. This versatile dihalogenation system—a combination of NX1S electrophile and alkali metal halide (MX2) in acetic acid—is applicable for diverse categories of alkynes (electron-rich or poor alkynes, internal and terminal alkynes, or heteroatoms such as O-, N-, S-substituted alkynes). The hydrogen bonding donor solvent acetic acid is essential for the in-situ generation of X1X2 electrophile, including ICl, IBr, BrCl, I2, and Br2. Haloalkenes are not only commonly found in biologically active natural products but also have been used extensively in cross-coupling reactions. More specifically, 1,2-dihaloalkenes are especially important synthons because of the presence of two synthetic handles that open a broad avenue to expeditiously generate multisubstituted alkenes. Dihalogenation of alkynes is a straightforward way to prepare 1,2-dihaloalkenes. However, existing alkyne dihalogenation methods either rely on the use of toxic reagents, such as IBr and ICl, lack regio- and stereoselectivity or have limited substrate scope. Thus, the development of a widely applicable and yet efficient alkyne dihalogenation method is still highly desired. Here, we have addressed the aforementioned issues based on an in-situ-generated dihalogenation of reagents, such as ICl and Ibr, by using the readily available N-halosuccinimide (NXS) and alkali metal halides as halogen sources. Our method offers an unprecedented substrate scope, the regio- and stereoselectivity for the synthesis of 1,2-dihaloalkenes. Our simple and mild conditions might find wild applications in the preparation of high-value building blocks for medicines and materials. Dihaloalkenes are important raw materials for pharmaceutical and chemical industries. However, existing preparation methods suffer from a limited substrate scope as well as poor regio- and stereoselectivity. Furthermore, these methods often necessitate highly toxic reagents, such as Cl2, ICl, and BrCl. Our environmentally friendly 1,2-trans-dihalogenation is based on easy-handling halide sources, such as alkali metal halides. What is more, our method offers an unprecedented substrate scope, the regio- and stereoselectivity for the synthesis of 1,2-dihaloalkenes.
Ready access to organoiodides: Practical hydroiodination and double-iodination of carbon-carbon unsaturated bonds with I2
Xiao, Jing,Han, Li-Biao
, p. 3510 - 3515 (2019/05/17)
By using I2 or I2/H3PO3 system, various alkenes and alkynes were converted to the corresponding alkyl and alkenyl iodides in good yields. In the presence of I2, alkynes could be di-iodinated using H2O as the solvent in air at room temperature. This method also features the simple work-up procedure since the pure product could be obtained by extraction. Additionally, for the first time, combining with the non-toxic and cheap phosphonic acid H3PO3, alkenes and alkynes were also hydroiodinated successfully, which provides a simple and practical approach for synthesis of organoiodides.
Chemoselective and stereospecific iodination of alkynes using sulfonium iodate(i) salt
Rao, Dodla S.,Reddy, Thurpu R.,Kashyap, Sudhir
, p. 1508 - 1518 (2018/03/08)
An efficient and highly chemoselective iodination of alkynes using a sulfonium iodate(i) electrophilc reagent under metal-free conditions has been realized. The reactivity of sulfonium iodate(i) salt could be significantly diverse in the presence of water
An aqueous medium-controlled stereospecific oxidative iodination of alkynes: Efficient access to (E)-diiodoalkene derivatives
Banothu, Rammurthy,Peraka, Swamy,Kodumuri, Srujana,Chevella, Durgaiah,Gajula, Krishna Sai,Amrutham, Vasu,Yennamaneni, Divya Rohini,Nama, Narender
supporting information, p. 17879 - 17883 (2018/11/21)
A new and versatile approach for the stereospecific iodination of alkynes using cheap, air stable and non-toxic reagents in aqueous media has been developed. This protocol is tolerant of various functional groups, and provides a broad range of vicinal diiodoalkenes with exceptional E-selectivity under mild conditions. Scale-up reactions (up to 5 g) established the proficiency of this protocol and highlight the feasibility of large scale reactions.
Cobalt-catalyzed stereoselective iodosulfonylation and diiodination of alkynes via oxidation of potassium iodide in air
Taniguchi, Nobukazu
, p. 1454 - 1460 (2018/02/15)
Cobalt-catalyzed iodosulfonylation of alkynes can be achieved using sodium sulfinates in the presence of KI. This procedure produces numerous stereoselective (E)-β-iodoalkenyl sulfones with good yields and suppresses the formation of diiodoalkenes. Furthermore, when this reaction is performed in the absence of sodium sulfinates, the expected (E)-diiodoalkenes are obtained.
One-Pot Synthesis of Trifluoromethylated Iodoisoxazoles via the Reaction of Trifluoroacetohydroximoyl Chloride with Terminal Alkynes and N -Iodosuccinimide
Guo, Yuwei,Wang, Xiaojun,Zhu, Zhentong,Zhang, Jianmin,Wu, Yongming
, p. 2259 - 2263 (2016/10/12)
Trifluoromethylated iodoisoxazoles have been synthesized by the reaction of trifluoroacetohydroximoyl chloride, alkynes, and N-iodosuccinimide in a one-pot reaction under metal-free and mild conditions. An array of iodoisoxazole compounds with a wide rang
(NH4)2S2O8-Mediated Diiodination of Alkynes with Iodide in Water: Stereospecific Synthesis of (E)-Diiodoalkenes
Jiang, Qing,Wang, Jing-Yu,Guo, Can-Cheng
, p. 2081 - 2087 (2015/07/15)
A new approach to the stereospecific diiodination of alkynes under mild conditions has been developed. This protocol employs ammonium persulfate as an oxidant and iodide as an iodine source, and provides a highly efficient and general method for the prepa
