Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal.

Title Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal.
Authors Y. Liu; S. Xiao; Y. Qi; F. Du
Journal Chem Asian J
DOI 10.1002/asia.201601712
Abstract

A homocoupling method for organohalides and organosulfonates promoted by samarium metal and HMPA, and catalyzed by NiCl2 has been developed. Various organohalides (benzyl, aryl, heterocyclic, alkenyl and alkyl halides), ?-haloacetophenones, and phenyl organosulfonates were tolerated, and the reaction afforded coupling products with high efficiency. Excellent chemoselectivity was exhibited between halides and other groups, such as -COOH, -NO2 , halogen, heterocyclic ring, ester, and ketone groups. The stereoselectivity suggested that the reaction mechanism might involve an organosamarium species.

Citation Y. Liu; S. Xiao; Y. Qi; F. Du.Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal.. Chem Asian J. 2017;12(6):673678. doi:10.1002/asia.201601712

Related Elements

Samarium

See more Samarium products. Samarium (atomic symbol: Sm, atomic number: 62) is a Block F, Group 3, Period 6 element with an atomic radius of 150.36. Samarium Bohr ModelThe number of electrons in each of samarium's shells is 2, 8, 18, 24, 8, 2 and its electron configuration is [Xe]4f6 6s2. The samarium atom has a radius of 180 pm and a Van der Waals radius of 229 pm. In its elemental form, samarium has a silvery-white appearance. Elemental Samarium PictureSamarium is not found as free element in nature. It is found in the minerals cerite, gadolinite, samarskite, monazite and bastnäsite. Samarium is classified as a rare earth element and is the 40th most abundant element in the Earth's crust. Samarium was discovered and first isolated by Lecoq de Boisbaudran in 1879. It is named after the mineral samarskite, the mineral from which it was isolated.

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.

Nickel

See more Nickel products. Nickel (atomic symbol: Ni, atomic number: 28) is a Block D, Group 4, Period 4 element with an atomic weight of 58.6934. Nickel Bohr ModelThe number of electrons in each of nickel's shells is [2, 8, 16, 2] and its electron configuration is [Ar]3d8 4s2. Nickel was first discovered by Alex Constedt in 1751. The nickel atom has a radius of 124 pm and a Van der Waals radius of 184 pm. In its elemental form, nickel has a lustrous metallic silver appearance. Nickel is a hard and ductile transition metal that is considered corrosion-resistant because of its slow rate of oxidation. Elemental NickelIt is one of four elements that are ferromagnetic and is used in the production of various type of magnets for commercial use. Nickel is sometimes found free in nature but is more commonly found in ores. The bulk of mined nickel comes from laterite and magmatic sulfide ores. The name originates from the German word kupfernickel, which means "false copper" from the illusory copper color of the ore.

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