76156-38-2Relevant academic research and scientific papers
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.
The Acid-Catalyzed Cyclization of Unsaturated Carbonyl Compounds Utilizing Silica Gel at High Pressure
Dauben, William G.,Hendricks, Robert T.
, p. 603 - 606 (2007/10/02)
The ene-like cyclizations of a series of unsaturated carbonyl compounds have been studied using silica gel at high pressure (15 kbar) as a new catalytic system.This new method is general for forming 5- and 6-membered ring carbocycles.The mildness of this
Alkylaluminum Halide Induced Cyclization of Unsaturated Carbonyl Compounds
Snider, Barry B.,Karras, Michael,Price, Robert T.,Rodini, David J.
, p. 4538 - 4545 (2007/10/02)
2,6-Dimethyl-5-heptenal (3) and 5-octenal (24) undergo concerted ene reactions with 1 equiv of Me2AlCl and cation-olefin cyclizations with 2 equiv of Me2AlCl, MeAlCl2, or EtAlCl2 to give a zwitterion which reacts to give several products including an ene
