501036-98-2Relevant academic research and scientific papers
Radical Transformation of Aliphatic C-H Bonds to Oxime Ethers via Hydrogen Atom Transfer
Wang, Xinmou,Yu, Mo,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 8353 - 8358 (2021/10/25)
Herein, we describe a strategy for conversion of aliphatic C-H bonds to oxime ethers via hydrogen atom transfer. In this strategy, the decatungstate anion and sulfate radical play complementary roles in the abstraction of hydrogen atoms from primary, secondary, and tertiary C-H bonds of alkanes. The easy accessibility of alkanes and the broad substrate scope, mild conditions, and excellent regioselectivity of these reactions make this strategy applicable for the transformation of raw materials to high-value chemicals.
Iridium(I)-Catalyzed α-C(sp3)-H Alkylation of Saturated Azacycles
Chekshin, Nikita,Qiao, Jennifer X.,Richter, Jeremy M.,Verma, Pritha,Yu, Jin-Quan
supporting information, p. 5117 - 5125 (2020/04/08)
Saturated azacycles are commonly encountered in bioactive compounds and approved therapeutic agents. The development of methods for functionalization of the α-methylene C-H bonds of these highly privileged building blocks is of great importance, especially in drug discovery. While much effort has been dedicated toward this goal by using a directed C-H activation approach, the development of directing groups that are both general as well as practical remains a significant challenge. Herein, the design and development of novel amidoxime directing groups is described for Ir(I)-catalyzed α-C(sp3)-H alkylation of saturated azacycles using readily available olefins as coupling partners. This protocol extends the scope of saturated azacycles to piperidines, azepane, and tetrahydroisoquinoline that are incompatible with our previously reported directing group. A variety of olefin coupling partners, including previously unreactive disubstituted terminal olefins and internal olefins, are compatible with this transformation. The selectivity for a branched α-C(sp3)-alkylation product is also observed for the first time when acrylate is used as the reaction partner. The development of practical, one-step installation and removal protocols further adds to the utility of amidoxime directing groups.
Radical-mediated synthesis of trifluoroethyl amines and trifluoromethyl ketones from alkyl iodides
Kim, Sunggak,Kavali, Rajesh
, p. 7189 - 7191 (2007/10/03)
Radical reaction of alkyl iodides with trifluoromethyl phenylsulfonyl oxime ether 10 and hexamethylditin at 300 nm in benzene afforded the corresponding trifluoromethyl oxime ethers 11 in high yields, which were reduced into the 2,2,2-trifluoroethyl amines with lithium aluminium hydride. The trifluoroethyl amines could be converted into the corresponding trifluoromethyl ketones by treatment with NBS and DBU.
