Tetrabutylammonium Iodide-Promoted Thiolation of Oxindoles Using Sulfonyl Chlorides as Sulfenylation Reagents.

Title Tetrabutylammonium Iodide-Promoted Thiolation of Oxindoles Using Sulfonyl Chlorides as Sulfenylation Reagents.
Authors X. Zhao; A. Wei; X. Lu; K. Lu
Journal Molecules
DOI 10.3390/molecules22081208
Abstract

3-Sulfanyloxindoles were synthesised by triphenylphosphine-mediated transition-metal-free thiolation of oxindoles using sulfonyl chlorides as sulfenylation reagents. The above reaction was promoted by iodide anions, which was ascribed to the in situ conversion of sulfenyl chlorides into the more reactive sulfenyl iodides. Moreover, the thiolation of 3-aryloxindoles was facilitated by bases. The use of a transition-metal-free protocol, readily available reagents, and mild reaction conditions make this protocol more practical for preparing 3-sulfanyloxindoles than traditional methods.

Citation X. Zhao; A. Wei; X. Lu; K. Lu.Tetrabutylammonium Iodide-Promoted Thiolation of Oxindoles Using Sulfonyl Chlorides as Sulfenylation Reagents.. Molecules. 2017;22(8). doi:10.3390/molecules22081208

Related Elements

Iodine

See more Iodine products. Iodine (atomic symbol: I, atomic number: 53) is a Block P, Group 17, Period 5 element with an atomic radius of 126.90447. The number of electrons in each of Iodine's shells is 2, 8, 18, 18, 7 and its electron configuration is [Kr] 4d10 5s2 5p5. The iodine atom has a radius of 140 pm and a Van der Waals radius of 198 pm. In its elemental form, iodine has a lustrous metallic gray appearance as a solid and a violet appearance as a gas or liquid solution. Elemental IodineIodine forms compounds with many elements, but is less active than the other halogens. It dissolves readily in chloroform, carbon tetrachloride, or carbon disulfide. Iodine compounds are important in organic chemistry and very useful in the field of medicine. Iodine was discovered and first isolated by Bernard Courtois in 1811. The name Iodine is derived from the Greek word "iodes" meaning violet.

Nitrogen

See more Nitrogen products. Nitrogen is a Block P, Group 15, Period 2 element. Its electron configuration is [He]2s22p3. Nitrogen is an odorless, tasteless, colorless and mostly inert gas. It is the seventh most abundant element in the universe and it constitutes 78.09% (by volume) of Earth's atmosphere. Nitrogen was discovered by Daniel Rutherford in 1772.

Chlorine

Chlorine is a Block P, Group 17, Period 3 element. Its electron configuration is [Ne]3s23p5. The chlorine atom has a covalent radius of 102±4 pm and its Van der Waals radius is 175 pm. Chlorine ModelIn its elemental form, chlorine is a yellow-green gas. Chlorine is the second lightest halogen after fluorine. It has the third highest electronegativity and the highest electron affinity of all elements, making it a strong oxidizing agent. It is rarely found by itself in nature. Chlorine was discovered and first isolated by Carl Wilhelm Scheele in 1774. It was first recognized as an element by Humphry Davy in 1808.

Related Forms & Applications