Transition-Metal-Free C(sp3)–H Coupling of Cycloalkanes Enabled by Single-Electron Transfer and Hydrogen Atom Transfer

• DOI: 10.1021/acs.orglett.1c00135
• Publication Date: 2021-02-17T18:37:40Z
• Authors: Linlin Zhang; Zhengfen Liu; Xun Tian; Yujin Zi; Shengzu Duan; Yongsheng Fang; Wen Chen; Hong Jing; Lijuan Yang; Xiaodong Yang
• Keywords: 2- azaallyls; Evolutionary Biology; cycloalkane-functionalized products; Chemical Sciences not elsewhere classified; Information Systems not elsewhere classified; Biophysics; Computational Biology; combination process; Unactivated cycloalkanes; Hydrogen Atom Transfer; Biochemistry; 01 natural sciences; transition metals; 0104 chemical sciences; Cycloalkanes Enabled; Environmental Sciences not elsewhere classified; Medicine; room temperature; single-electron transfer; Molecular Biology; Physical Sciences not elsewhere classified; Biological Sciences not elsewhere classified

Here we report a unique transition-metal-free C(sp3)-H/C(sp3)-H coupling of cycloalkanes at room temperature. Unactivated cycloalkanes and 2-azaallyls underwent the combination process of single-electron transfer (SET) and hydrogen atom transfer (HAT) to deliver a wide variety of cycloalkane-functionalized products. This expedient approach enables C(sp3)-H/C(sp3)-H coupling of cycloalkanes under mild conditions without transition metals, initiators, and oxidants.