161618-48-0Relevant academic research and scientific papers
δ-C-H Mono- And Dihalogenation of Alcohols
Herron, Alastair N.,Liu, Dongxin,Xia, Guoqin,Yu, Jin-Quan
, p. 2766 - 2770 (2020/02/13)
Alkoxy radicals have long been known to enable remote C-H functionalization via 1,5-hydrogen atom abstraction. However, methods for their generation traditionally have relied upon highly oxidizing metals, ultraviolet radiation, or preformed peroxide intermediates, which has prevented the development of many desirable transformations. Herein we report a new bench-stable precursor that decomposes to free alkoxy radicals via a previously unreported single-electron oxidation pathway. This new precursor enables the fluorination and chlorination of remote C-H bonds under exceptionally mild conditions with exceedingly high monoselectivity. Iterative use of this precursor enables the introduction of a second halogen atom, granting access to remote dihalide motifs, including CF2 and CFCl.
Iron(II)-Catalyzed Site-Selective Functionalization of Unactivated C(sp3)?H Bonds Guided by Alkoxyl Radicals
Guan, Honghao,Sun, Shutao,Mao, Ying,Chen, Lei,Lu, Ran,Huang, Jiancheng,Liu, Lei
supporting information, p. 11413 - 11417 (2018/08/28)
An alkoxyl radical guided strategy for site-selective functionalization of unactivated methylene and methine C?H bonds enabled by an FeII-catalyzed redox process is described. The mild, expeditious, and modular protocol allows efficient remote aliphatic fluorination, chlorination, amination, and alkynylation of structurally and electronically varied primary, secondary, and tertiary hydroperoxides with excellent functional-group tolerance. The application for one-pot 1,4-hydroxyl functionalization of non-oxygenated alkane substrates initiated by aerobic C?H oxygenation is also demonstrated.
A catalytic stereo- and chemo-selective method for the reduction of substituted aromatics
Fache,Lehuede,Lemaire
, p. 885 - 888 (2007/10/02)
Various substituted aromatics have been reduced using colloidal ruthenium under H2 pressure with good stereoselectivity (cis/trans up to 60). Interesting chemoselectivities are also observed.
