38089-02-0Relevant articles and documents
Scalable electrochemical synthesis of diaryliodonium salts
Elsherbini, Mohamed,Moran, Wesley J.
supporting information, p. 4706 - 4711 (2021/06/11)
Cyclic and acyclic diaryliodonium are synthesised by anodic oxidation of iodobiaryls and iodoarene/arene mixtures, respectively, in a simple undivided electrolysis cell in MeCN-HFIP-TfOH without any added electrolyte salts. This atom efficient process does not require chemical oxidants and generates no chemical waste. More than 30 cyclic and acyclic diaryliodonium salts with different substitution patterns were prepared in very good to excellent yields. The reaction was scaled-up to 10 mmol scale giving more than four grams of dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (>95%) in less than three hours. The solvent mixture of the large-scale experiment was recovered (>97%) and recycled several times without significant reduction in yield.
Electrochemical Palladium-Catalyzed Intramolecular C—H Amination of 2-Amidobiaryls for Synthesis of Carbazoles
Gao, Xinlong,Lei, Aiwen,Wang, Pan,Wang, Qingqing,Zhang, Heng,Zhang, Xiaojing
supporting information, p. 143 - 148 (2020/12/18)
The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C—H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.
Photocatalytic xanthate-based radical addition/cyclization reaction sequence toward 2-biphenyl isocyanides: Synthesis of 6-alkylated phenanthridines
López-Mendoza, Pedro,Miranda, Luis D.
supporting information, p. 3487 - 3491 (2020/05/25)
A photocatalytic xanthate-based radical addition/cyclization reaction cascade toward 2-biphenylisocyanides is described as a practical and modular approach to 6-alkylated phenanthridines. The use of xanthates as radical precursors allowed the synthesis of diversely 6-substituted phenanthridines. Electrophilic radicals derived from nitriles, aromatic and aliphatic ketones, malonates, and amide derivatives, as well as radicals derived from phthalimidomethyl and benzylic derivatives were successfully introduced. The reaction proceeds under mild conditions without a stoichiometric amount of oxidant. Thirty novel phenanthridine scaffolds were synthesized with yields ranging from 24 to 76%.
