Photodecarboxylative Amination of Redox-Active Esters with Diazirines

2021 ◽  
Author(s):  
Vishala Maharaj ◽  
Preeti P. Chandrachud ◽  
Wen Che ◽  
Lukasz Wojtas ◽  
Justin M. Lopchuk
Keyword(s):  
Active Esters ◽  
Redox Active

scholarly journals Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids

2016 ◽  
Vol 55 (33) ◽  
pp. 9676-9679 ◽  
Author(s):  
Jie Wang ◽  
Tian Qin ◽  
Tie-Gen Chen ◽  
Laurin Wimmer ◽  
Jacob T. Edwards ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Active Esters ◽  
Redox Active

Decarboxylative Thiolation of Redox-Active Esters to Thioesters by Merging Photoredox and Copper Catalysis

2020 ◽  
Vol 22 (9) ◽  
pp. 3692-3696
Author(s):  
Tianxiao Xu ◽  
Tianpeng Cao ◽  
Mingcheng Yang ◽  
Ruting Xu ◽  
Xingliang Nie ◽  
...  
Keyword(s):  
Copper Catalysis ◽  
Active Esters ◽  
Redox Active

scholarly journals Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters

2019 ◽  
Vol 10 (3) ◽  
pp. 809-814 ◽  
Author(s):  
Xi Lu ◽  
Xiao-Xu Wang ◽  
Tian-Jun Gong ◽  
Jing-Jing Pi ◽  
Shi-Jiang He ◽  
...  
Keyword(s):  
Active Esters ◽  
Redox Active

Synthesis of functionalized gem-difluoroalkenes was achieved through nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters.

scholarly journals Practical Ni-Catalyzed Aryl–Alkyl Cross-Coupling of Secondary Redox-Active Esters

2016 ◽  
Vol 138 (7) ◽  
pp. 2174-2177 ◽  
Author(s):  
Josep Cornella ◽  
Jacob T. Edwards ◽  
Tian Qin ◽  
Shuhei Kawamura ◽  
Jie Wang ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Active Esters ◽  
Redox Active

scholarly journals Transition metal-free photodecarboxylative amination of redox-active esters with diazirines

2021 ◽  
Author(s):  
Vishala Maharaj ◽  
Preeti Chandrachud ◽  
Wen Che ◽  
Lukasz Wojtas ◽  
Justin Lopchuk
Keyword(s):  
Transition Metal ◽  
Blue Light ◽  
Electrophilic Amination ◽  
Metal Free ◽  
Active Esters ◽  
Mild Conditions ◽  
Redox Active ◽  
The Stability ◽  
Nitrogen Containing Compounds ◽  
Intense Research

Due to the prevalence of nitrogen-containing compounds in medicine, materials, and related fields, the search for general, mild methods for electrophilic amination remains an area of intense research. Diazirines have been recently demonstrated to serve as electrophilic amination reagents that afford diaziridines, versatile heterocycles that are readily transformed into amines, hydrazines, and a variety of nitrogen-containing heterocycles. Here we report the phosphine-mediated, photodecarboxylative amination of redox-active esters with diazirines. This method is transition metal-free, uses inexpensive photoactivators under mild conditions, and offers a significantly enhanced scope and yields for primary redox-active esters. Furthermore, the stability of diazirines to blue light (456 nm) is demonstrated, paving the way for further research into other photochemical amination methods with these unique heterocycles.

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