Photocatalytic Reductive Azaarenylation of Cyclopropanes via Consecutive Photo-induced Electron Transfer: A Facile Route to α-Quaternary Azaarenes
Gaolei Sun , Wenhui Wei , Xiaowei Zhao , Baokun Qiao , Zhiyong Jiang
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (23) : 3035 -3040.
Photocatalytic Reductive Azaarenylation of Cyclopropanes via Consecutive Photo-induced Electron Transfer: A Facile Route to α-Quaternary Azaarenes
α-Azaarene quaternary carbon centers are prevalent in drug molecules, making the development of efficient synthetic approaches of great interest. Herein, we describe an unprecedented method for constructing α-all-carbon quaternary carbon-centered azaarenes by employing photocatalytic reductive coupling of various 2, 2-disubstituted cycloproarylketones with readily available cyanoazaarenes. The reaction proceeds with high efficiency, displaying excellent compatibility with various functional groups and demonstrating high chemo- and regioselectivity. Mechanistic investigations suggest that consecutive photo-induced electron transfer (ConPET) plays a crucial role in the formation of photocatalyst with greater reducing capability, ultimately enabling the direct reductive conversion of unreactive π-bonds under mild and transition-metal-free conditions.
Photoredox catalysis / Reductive azaarenylation / ConPET / Cross-coupling / Radical reactions / N-Heterocycles
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
