53279-82-6Relevant academic research and scientific papers
Entry to 1,2,3,4-Tetrasubstituted Arenes through Addressing the " Meta Constraint" in the Palladium/Norbornene Catalysis
Dong, Guangbin,Liu, Peng,Wang, Jianchun,Xu, Xiaolong,Zhou, Yun
supporting information, p. 3050 - 3059 (2020/03/10)
Arenes with four different contiguous substituents, i.e. 1,2,3,4-tetrasubstituted arenes, are commonly found in bioactive compounds, but they are nontrivial to access via conventional methods. Through addressing the "meta constraint" in the palladium/norbornene (Pd/NBE) cooperative catalysis, which is the difficulty of tolerating a sizable meta substituent in aryl halide substrates, here a modular and regioselective approach is realized for preparing 1,2,3,4-tetrasubstituted arenes. One key is the use of a C2-amide-substituted NBE, and a combined experimental and computational study reveals its role in promoting the NBE insertion and the ortho C-H metalation steps. The scope is broad: A variety of electrophiles and nucleophiles could be introduced to the ortho and ipso positions, respectively, with 1,4-disubstituted aryl halides, leading to diverse unsymmetrical contiguous tetrasubstituted arenes. Application of this approach has been demonstrated in streamlined syntheses of several bioactive compounds.
Pd-catalyzed atom-efficient cross-coupling of triarylbismuth reagents with protecting group-free iodophenylmethanols: Synthesis of biarylmethanols
Meka, Suresh,Rao, Maddali L. N.
supporting information, (2020/02/11)
An atom-efficient procedure for the synthesis of functionalized biarylmethanols via the Pd-catalyzed cross-coupling reactions of differently functionalized iodophenylmethanols and triarylbismuth reagents is described. This protecting group-free direct couplings of 2-, 3- or 4-iodophenylmethanols with triarylbismuth reagents afforded biarylmethanols in good to high yields.
Effect of water on the functionalization of substituted anisoles with iodine in the presence of F-TEDA-BF4 or hydrogen peroxide
Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
, p. 1027 - 1032 (2007/10/03)
Water was found to be a convenient reaction medium for functionalization of substituted anisoles using iodine in the presence of Selectfluor F-TEDA-BF 4 or hydrogen peroxide as mediators and oxidizers. Two types of functionalization were observ
Tetramethylammonium dichloroiodate: An efficient and environmentally friendly iodination reagent for iodination of aromatic compounds under mild and solvent-free conditions
Hajipour, Abdol R.,Arbabian, Marty,Ruoho, Arnold E.
, p. 8622 - 8624 (2007/10/03)
Tetramethylammonium dichloroiodate (1, TMADCI) as a mild and efficient iodination reagent was prepared. Iodination of different aromatic compounds with this reagent takes place fast and with high yields under solvent-free conditions.
N-iodosaccharin - A new reagent for iodination of alkenes and activated aromatics
Dolenc, Darko
, p. 544 - 546 (2007/10/03)
A mild and efficient iodination reagent, N-iodosaccharin was prepared. Iodination of activated aromatics and alkenes with the reagent takes place fast and under very mild conditions, without the aid of strong acids or heavy metals. The reagent does not affect oxidizable groups, such as hydroxyl or aldehyde.
