4096-21-3Relevant articles and documents
Metal-free protocol for the synthesis of N-arylpyrrolidines catalyzed by hydrogen iodine
Hou, Tingting,Zhang, Chaofeng,Wang, Yehong,Liu, Zhenting,Zhang, Zhixin,Wang, Feng
, p. 56 - 59 (2017)
A metal-free and efficient approach to N-arylpyrrolidines from arylamines and cyclic ethers catalyzed by hydrogen iodine is described. In this protocol, no additive is added and a wide range of N-arylpyrrolidines are synthesized with up to 99% yield. Reaction mechanism involving iodine radical is proposed.
Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups
Amberchan, Gabriella,Snelling, Rachel A.,Moya, Enrique,Landi, Madison,Lutz, Kyle,Gatihi, Roxanne,Singaram, Bakthan
supporting information, p. 6207 - 6227 (2021/05/06)
The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.
Dual Photoredox/Cobaloxime Catalysis for Cross-Dehydrogenative α-Heteroarylation of Amines
Bergamaschi, Enrico,Weike, Christopher,Mayerhofer, Victor J.,Funes-Ardoiz, Ignacio,Teskey, Christopher J.
supporting information, p. 5378 - 5382 (2021/07/26)
We report a dual-catalytic platform for the cross-dehydrogenative-coupling between (benzo-)thiazoles and amines which combines low loadings of an iridium photoredox catalyst and a cobaloxime catalyst under blue light irradiation. This transformation occurs without stoichiometric oxidants, giving products in moderate to excellent yields. DFT calculations support the key role of Co(II) for rearomatization of the radical-addition intermediate to generate the product.
Reduced Phenalenyl in Catalytic Dehalogenative Deuteration and Hydrodehalogenation of Aryl Halides
Singh, Bhagat,Ahmed, Jasimuddin,Biswas, Amit,Paira, Rupankar,Mandal, Swadhin K.
, p. 7242 - 7255 (2021/05/29)
Dehalogenative deuteration reactions are generally performed through metal-mediated processes. This report demonstrates a mild protocol for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides (39 examples) using a reduced odd alternant hydrocarbon phenalenyl under transition metal-free conditions and has been employed successfully for the incorporation of deuterium in various biologically active compounds. The combined approach of experimental and theoretical studies revealed a single electron transfer-based mechanism.
