125610-78-8Relevant articles and documents
A Foldamer-Based Organocatalyst for Direct Arylations of Unactivated Arenes
Zhao, Huaiqing,Shen, Jie,Ren, Changliang,Zeng, Wei,Zeng, Huaqiang
, p. 2190 - 2193 (2017)
It was demonstrated that a simple yet well-folded pyridone dimer, possessing two convergently aligned electron-rich O atoms for potassium binding, can serve as a highly efficient organocatalyst for catalyzing transition-metal-free arylations of unactivated aromatic C-H bonds with aryl halides in the presence of t-BuOK. A wide range of aryl iodides could be cross-coupled with unactivated arenes in moderate to excellent yields. The experiments using radical-scavenging reagents confirm the participation of radicals in this catalytic transformation.
Preparation of Functionalized Diorganomagnesium Reagents in Toluene via Bromine or Iodine/Magnesium-Exchange Reactions
Desaintjean, Alexandre,Danton, Fanny,Knochel, Paul
supporting information, p. 4461 - 4476 (2021/08/13)
A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents are prepared in toluene within 10 to 120 minutes between 78 C and 25 C via an I/Mg- or Br/Mg-exchange reaction using reagents of the general formula R2Mg (R = sBu, Mes). Highly sensitive functional groups, such as triazene or nitro, are tolerated in these exchange reactions, enabling the synthesis of various functionalized (hetero)arene and alkene derivatives after quenching with several electrophiles including allyl bromides, acyl chlorides, aldehydes, ketones, and aryl iodides.
Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone
Bracher, Franz,Jourjine, Ilya A. P.,Krau?, Jürgen,Zeisel, Lukas
supporting information, p. 2668 - 2679 (2021/11/30)
Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.
6-Arylphenanthridines from Aryl o-Biaryl Ketones with 1,1,1,3,3,3-Hexamethyldisilazane and Molecular Iodine
Kobayashi, Eiji,Kishi, Atsushi,Togo, Hideo
, p. 7335 - 7347 (2019/11/22)
Warming treatment of aryl o-biaryl ketones with 1,1,1,3,3,3-hexamethyldisilazane in the presence of Sc(OTf)3 in toluene, followed by the reaction with molecular iodine and K2CO3 in a mixture of THF and methanol at 60 °C gave the corresponding 6-arylphenanthridines in good to moderate yields. The present reaction is a one-pot method for the preparation of 6-arylphenanthridines from aryl o-biaryl ketones through the cyclization of imino-nitrogen-centered radicals that were generated from N-iodo aryl o-biaryl ketimines formed from the reaction of aryl biaryl ketimines with molecular iodine.