Yajing Lian's research while affiliated with ACG Worldwide and other places

Publications (2)

Article
Full-text available
C–F functionalization of arenes with a range of alcohol and pyrazole nucleophiles has been achieved without the need for metal catalysts or highly electron‐poor substrates. Treatment of fluoroarenes with alcohols or pyrazoles and DDQ under irradiation by blue LED light provides the corresponding substituted products. The procedure is complementary...
Article
A metal-free photoredox C–H alkylation of heteroaromatics from readily available carboxylic acids using an organic photocatalyst and hypervalent iodine reagents under blue LED light is reported. The developed methodology tolerates a broad range of functional groups and can be applied to the late-stage functionalization of drugs and drug-like molecu...

Citations

... Since the oxidation potentials of unactivated or deactivated olefins or arenes lie at (or beyond) the energy threshold of single-photon PRC, the development of highly oxidizing photocatalysts is highly desirable to provide access to facile functionalization of these important and abundant feedstock chemicals. While it has been demonstrated that classical chemical oxidant 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) can function as a closed-shell photocatalyst with an excited-state reduction potential ≈+3 V vs SCE and can oxidatively engage elec-tron-deficient arenes [124,125], the application of DDQ is rather undesirable due to the requirement for larger catalyst loadings (10-20 mol %) [126], the use of tert-butyl nitrite co-oxidant that forms explosive mixtures in air, evolution of HCN gas upon contact with moisture [127] and catalyst degradation via side reactions with certain amines under the reaction conditions [124]. These limitations are easily overcome by i) oxidative conPET or ii) the merging of photo-and electrochemistry through the use of anodic oxidation (vide infra, especially for DDQ) and the former will now be presented. ...
... In 2018, Frenette and colleagues developed an organophotocatalytic CÀ H alkylation method for quinolines using an acridinium salt (PC8) as the photoredox catalyst and aliphatic carboxylic acids as alkylating reagents (Scheme 26). [59] In one example, the reaction of 4-methylquinoline (15 a) with acetic acid (40) proceeded smoothly, yielding 2,4-dimethylquinoline (16 a) in a 43 % yield, demonstrating its effectiveness in CÀ H methylation. ...