More Like this

1. Ni-Electrocatalytic C(sp3)–C(sp3) Doubly Decarboxylative Coupling

   https://doi.org/10.1038/s41586-022-04691-4  

   Zhang, Benxiang; Gao, Yang; Hioki, Yuta; Oderinde, Martins S.; Qiao, Jennifer X.; Rodriguez, Kevin X.; Zhang, Hai-Jun; Kawamata, Yu; Baran, Phil S. (April 2022, Nature)
2. Electrochemical C(sp3)–H Fluorination

   https://doi.org/10.1055/s-0037-1611737  

   Takahira, Yusuke; Chen, Miao; Kawamata, Yu; Mykhailiuk, Pavel; Nakamura, Hugh; Peters, Byron K.; Reisberg, Solomon H.; Li, Chao; Chen, Longrui; Hoshikawa, Tamaki; et al (May 2019, Synlett)

   A simple and robust method for electrochemical alkyl C–H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C–H bonds are converted into their C–F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline. 

   more » « less
3. Copper Catalyzed sp3 C-H a-Acetylation

   https://doi.org/10.26434/chemrxiv.11407116  

   Okoromoba, O; Jang, E.S.; McMullin, C.; Cundari, T. R.; Warren, T. H. (December 2019, ChemRxiv)

   null (Ed.)

   α-substituted ketones are important chemical targets as synthetic intermediates as well as functionalities in in natural products and pharmaceuticals. We report the sp3 C-H α-acetylation of sp3 C-H substrates R-H with arylmethyl ketones ArC(O)Me to provide α-alkylated ketones ArC(O)CH2R at RT with tBuOOtBu as oxidant via copper(I) β-diketiminato catalysts. Proceeding via alkyl radicals R•, this method enables α-substitution with bulky substituents without competing elimination that occurs in more traditional alkylation reactions between enolates and alkyl electrophiles. DFT studies suggest the intermediacy of copper(II) enolates [CuII](CH2C(O)Ar) that capture alkyl radicals R• to give R-CH2C(O)Ar under competing dimerization of the copper(II) enolate to give the 1,4-diketone ArC(O)CH2CH2C(O)Ar. 

   more » « less
4. Photoredox catalyzed C(sp3) C(sp) coupling of dihydropyridines and alkynylbenziodoxolones

   https://doi.org/10.1016/j.tetlet.2019.151230  

   Liang, Shengzong; Angnes, Ricardo A.; Potnis, Chinmay S.; Hammond, Gerald B. (November 2019, Tetrahedron Letters)
5. Three-dimensional saturated C(sp3)-rich bioisosteres for benzene

   https://doi.org/10.1038/s41570-024-00623-0  

   Tsien, Jet; Hu, Chao; Merchant, Rohan R; Qin, Tian (August 2024, Nature Reviews Chemistry)