126501-63-1

Upstream product

• 127-09-3 sodium acetate 
• 536-74-3 phenylacetylene 
• 6540-76-7 iodine monoacetate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

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.

Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes

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.

Selective oxygenation of alkynes: A direct approach to diketones and vinyl acetate

Arylalkynes can be converted into α-diketones with the use of a copper catalyst, and also be transformed into vinyl acetates under metal-free conditions, both in the presence of PhI(OAc)2 as an oxidant at room temperature. A series of substituted α-diketones were prepared in moderate to good yields. A variety of vinyl halides could be regio- and stereo-selectively synthesized under mild conditions, and I, Br and Cl could be all easily embedded into the alkynes. This journal is

Electrophilic Additions of Positive Iodine to Alkynes through an Iodonium Mechanism

Alkynes react with bis(pyridine)iodonium (I) tetrafluoroborate (1) and nucleophiles (CH3COOH, HCOOH, Cl-, pyridine, Br-, I-) to give 1,2 iodofunctionalized alkenes.The regiochemistry of the processes is in accordance with