70129-83-8Relevant academic research and scientific papers
Photocatalytic Oxidative Iodination of Electron-Rich Arenes
Narobe, Rok,Düsel, Simon J. S.,Iskra, Jernej,K?nig, Burkhard
supporting information, p. 3998 - 4004 (2019/07/17)
A visible-light-mediated oxidative iodination of electron-rich arenes has been developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeds upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly coloured iodine solutions can be observed at around 400 nm. The method provides good to excellent yields (up to 98%) and shows excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. (Figure presented.).
Rhenium-Catalyzed Cyclization via 1,2-Iodine and 1,5-Hydrogen Migration for the Synthesis of 2-Iodo-1 H-indenes
Murai, Masahito,Takai, Kazuhiko
supporting information, p. 6756 - 6760 (2019/08/26)
A rhenium complex catalyzed the formation of 2-iodo-1H-indene derivatives through iodine and hydrogen migration of 3-iodopropargyl ethers. The reaction proceeded via generation of 1-iodoalkenylrhenium carbene species by sequential 1,2-iodine and 1,5-hydro
An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides
Banik, Trisha,Betkekar, Vipul V.,Kaliappan, Krishna P.
supporting information, p. 3676 - 3680 (2018/10/31)
A direct transformation of ortho-alkynylated aromatic vinyl ethers to 1-iodonaphthalenes and other iodo-heterocycles under mild Lewis acidic conditions in the presence of iodide as an external nucleophile is reported. The first example of an iodoannulation strategy using a nucleophilic source of iodine, coupled with good to excellent yields, exclusive alpha regioselectivity and a broad substrate scope makes this work an attractive avenue towards the construction of aromatic iodides.
Catalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation-Directed Nucleophilic Aromatic Substitution Reaction
Armstrong, Roly J.,Smith, Martin D.
supporting information, p. 12822 - 12826 (2016/02/18)
A catalytic enantioselective nucleophilic aromatic substitution reaction which yields axially chiral biaryl derivatives in excellent yields with e.r. values of up to 97:3 has been developed. This process uses a chiral counterion to direct the addition of thiophenolate to a prochiral dichloropyrimidine by a tandem desymmetrization/kinetic resolution mechanism. The products can be derivatized to a range of atropisomeric structures without any reduction in enantioenrichment, thus offering access to unexplored chiral biaryl architectures.
Efficient and direct iodination of alkyl benzenes using polymer/HIO4 and I2 under mild condition
Bahrami-Nasab, Sepideh,Nazifi, S. Mohamad Reza,Pourali, Ali Reza
, p. 305 - 308 (2014/06/24)
An efficient and rapid method has been found for the iodination of aromatic compounds using iodine and polymer-supported periodic acid (PSPIA) as an oxidant under mild aprotic conditions. The reagent after the completion of the reaction was easily removed by filtration and was regenerated for further use. This method has some advantages such as: mild reaction conditions, straight forward procedure, inexpensive method, high yields and one-pot conversion.
Reactions of iodinated vinylidene complexes generated from 1-Iodo-1-alkynes and W(CO)5(thf)
Miura, Tomoya,Iwasawa, Nobuharu
, p. 518 - 519 (2007/10/03)
We have succeeded in generating iodinated tungsten vinylidene complexes from 1-iodo-1-alkynes and W(CO)5(thf), and have employed these complexes for two types of synthetically useful reactions, that is, 6π-electrocyclization for o-(iodoethynyl)
