Visible Light-Driven Radical-Mediated C–C Bond Cleavage/Functionalization in Organic Synthesis

Author(s):  
Xiao-Ye Yu ◽  
Jia-Rong Chen ◽  
Wen-Jing Xiao
SynOpen ◽  
2019 ◽  
Vol 03 (04) ◽  
pp. 103-107 ◽  
Author(s):  
Penghua Shu ◽  
Haichang Xu ◽  
Lingxiang Zhang ◽  
Junping Li ◽  
Hao Liu ◽  
...  

(Z)-Cinnamate derivatives are prevalent in natural bioactive products and in organic synthesis. Herein, we report a practical approach toward the efficient synthesis of (Z)-cinnamate derivatives via visible-light-driven isomerization. When E-isomers of cinnamate derivatives were irradiated with blue light in the presence of 1 mol% Ir2(ppy)4Cl2 (ppy = 2-phenylpyridine), Z-isomers were readily obtained in good yields. This strategy allows the large-scale synthesis of (Z)-cinnamate derivatives with simple purification. This convenient, mild, and green synthetic methodology was subsequently applied to the synthesis of coumarins.


2019 ◽  
Vol 21 (7) ◽  
pp. 1994-1998 ◽  
Author(s):  
Kai Wei ◽  
Kai Luo ◽  
Fang Liu ◽  
Lei Wu ◽  
Li-Zhu Wu

2018 ◽  
Vol 57 (3) ◽  
pp. 738-743 ◽  
Author(s):  
Xiao‐Ye Yu ◽  
Jia‐Rong Chen ◽  
Peng‐Zi Wang ◽  
Meng‐Nan Yang ◽  
Dong Liang ◽  
...  

2017 ◽  
Vol 130 (3) ◽  
pp. 746-751 ◽  
Author(s):  
Xiao‐Ye Yu ◽  
Jia‐Rong Chen ◽  
Peng‐Zi Wang ◽  
Meng‐Nan Yang ◽  
Dong Liang ◽  
...  

2019 ◽  
Vol 55 (79) ◽  
pp. 11888-11891 ◽  
Author(s):  
Yong-Hong Li ◽  
Chun-Hai Wang ◽  
Su-Qian Gao ◽  
Feng-Ming Qi ◽  
Shang-Dong Yang

A novel oxime phosphonate was synthesized and used in the difunctionalization of alkenes to access β-functionalized phosphonates via visible-light-driven N-centered iminyl radical-mediated multiple bond cleavage and a recombination process.


2021 ◽  
Author(s):  
Bhisma K. Patel ◽  
Tipu Alam ◽  
Amitava Rakshit

In the last few years, the photo-redox process via single-electron transfer (SET) has received substantial attention for the synthesis of targeted organic compounds due to its environmental friendliness and sustainability. Of late visible-light-mediated difunctionalization of alkenes has gained much attention because of its step economy, which allows the consecutive installation of two functional groups across the C=C bond in a single operation. The construction of N-containing compounds has always been important in organic synthesis. Molecules containing C-N bonds are found in many building blocks and are important precursors to other functional groups. Meanwhile, C-N bond formation via the addition of the C=C double bond is gaining prominence. Therefore, considering the influence and synthetic potential of the C-N bond, here we provide a summary of the state of the art on visible-light-driven difunctionalizations of alkene. We hope that the construction of the C-N bond via visible-light-mediated difunctionalization of alkenes will be useful for medicinal and synthetic organic chemists and will inspire further reaction development in this interesting area.


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