Xu, Jinhui; Cao, Jilei; Wu, Xiangyang; Wang, Han; Yang, Xiaona; Tang, Xinxin; Toh, Ren Wei; Zhou, Rong; Yeow, Edwin K. L.; Wu, Jie published the artcile< Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides>, Product Details of C13H19BO3, the main research area is aryl chloride boronate light cyanoarene photoreductive borylation catalyst; arylboronate preparation; phosphine aryl chloride light cyanoarene phosphorylation catalyst; arylphosphonium salt preparation.
Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN•-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.
Journal of the American Chemical Society published new progress about Aromatic nitriles Role: CAT (Catalyst Use), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Product Details of C13H19BO3.
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem