70-11-1Relevant articles and documents
Simultaneous multistep synthesis using polymeric reagents
Parlow, John J.
, p. 1395 - 1396 (1995)
A synthesis was accomplished involving three transformations using three different polymeric reagents simultaneously in one reaction vessel to afford 2-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-1-pheny lethanone (4).
Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst
Bennett, Elliot L.,Brookfield, Adam,Guan, Renpeng,Huang, Zhiliang,Mcinnes, Eric J. L.,Robertson, Craig M.,Shanmugam, Muralidharan,Xiao, Jianliang
supporting information, p. 10005 - 10013 (2021/07/19)
The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.
A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions
Wang, Zhihui,Wang, Lei,Wang, Zhiming,Li, Pinhua,Zhang, Yicheng
supporting information, p. 429 - 432 (2020/02/29)
A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.
