1078-36-0Relevant articles and documents
Palladium(0)-catalyzed iminohalogenation of alkenes: Synthesis of 2-halomethyl dihydropyrroles and mechanistic insights into the alkyl halide bond formation
Chen, Chen,Hou, Longlei,Cheng, Mian,Su, Jianhua,Tong, Xiaofeng
, p. 3092 - 3096 (2015)
Although the advances on carbon halide reductive elimination have been made, the alkyl bromide and chloride analogues remain a challenge. Here, a palladium(0)-catalyzed iminohalogenation of γ,δ-unsaturated oxime esters is described, and the use of electron-poor phosphine ligands proved to be crucial to promoting alkyl bromide and chloride reductive elimination. Furthermore, SN2-type alkyl bromide and chloride reductive elimination has also been established.
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
, 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.
Iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes
Tian, Tian,Wang, Xin,Lv, Leiyang,Li, Zhiping
, p. 14637 - 14640 (2020/12/02)
Herein, an iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes via distal group ipso-migration is reported. This strategy overcame the energy barrier and reversibility in the difunctionalization of unactivated alkenes with nuc
