4170-72-3Relevant articles and documents
Roggero et al.
, p. 313,316, 319 (1979)
Iodosylbenzene Coordination Chemistry Relevant to Metal-Organic Framework Catalysis
Cardenal, Ashley D.,Maity, Asim,Gao, Wen-Yang,Ashirov, Rahym,Hyun, Sung-Min,Powers, David C.
supporting information, p. 10543 - 10553 (2019/09/13)
Hypervalent iodine compounds formally feature expanded valence shells at iodine. These reagents are broadly used in synthetic chemistry due to the ability to participate in well-defined oxidation-reduction processes and because the ligand-exchange chemist
Fundamental Difference in Reductive Lithiations with Preformed Radical Anions versus Catalytic Aromatic Electron-Transfer Agents: N,N-Dimethylaniline as an Advantageous Catalyst
Kennedy, Nicole,Liu, Peng,Cohen, Theodore
supporting information, p. 383 - 386 (2016/01/25)
The reductive lithiation of phenyl thioethers, or alkyl chlorides, by either preformed aromatic radical anions or by lithium metal and an aromatic electron-transfer catalyst, is commonly used to prepare organolithiums. Revealed herein is that these two methods are fundamentally different. Reductions with radical anions occur in solution, whereas the catalytic reaction occurs on the surface of lithium, which is constantly reactivated by the catalyst, an unconventional catalyst function. The order of relative reactivity is reversed in the two methods as the dominating factor switches from electronic to steric effects of the alkyl substituent. A catalytic amount of N,N-dimethylaniline (DMA) and Li ribbon can achieve reductive lithiation. DMA is significantly cheaper than alternative catalysts, and conveniently, the Li ribbon does not require the removal of the oxide coating when DMA is used as the catalyst.
