38430-55-6Relevant articles and documents
Alkoxycarbonylation reactions performed using near-stoichiometric quantities of CO
Kormos, Chad M.,Leadbeater, Nicholas E.
, p. 2006 - 2010 (2007)
Alkoxycarbonylation reactions using near-stoichiometric quantities of carbon monoxide gas are presented. The reactions are performed using microwave heating which, as well as the inherent advantages of rate acceleration, offers a convenient method for loading vessels with gases. Georg Thieme Verlag Stuttgart.
Application of a batch microwave unit for scale-up of alkoxycarbonylation reactions using a near-stoichiometric loading of carbon monoxide
Iannelli, Mauro,Bergamelli, Fabio,Kormos, Chad M.,Paravisi, Stefano,Leadbeater, Nicholas E.
, p. 634 - 637 (2009)
The ethoxycarbonylation of iodobenzene was performed on the 1 mol scale in batch mode using microwave heating. The reaction was performed using both an excess and a near stoichiometric loading of carbon monoxide, comparable yields being obtained. Six different alkoxycarbonylation reactions were then performed simultaneously on the 50 mmol scale using a near-stoichiometric loading of carbon monoxide with excellent conversions in each case.
Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis
García Manche?o, Olga,Kuhlmann, Jan H.,Pérez-Aguilar, María Carmen,Piekarski, Dariusz G.,Uygur, Mustafa
supporting information, p. 3392 - 3399 (2021/05/21)
A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.
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.
