Combining Oxoammonium Cation Mediated Oxidation and Photoredox Catalysis for the Conversion of Aldehydes into Nitriles

Synlett ◽  
2018 ◽  
Vol 29 (16) ◽  
pp. 2185-2190 ◽  
Author(s):  
Nicholas Leadbeater ◽  
Jyoti Nandi ◽  
Mason Witko

A method to oxidize aromatic aldehydes to nitriles has been developed. It involves a dual catalytic system of 4-acetamido-TEMPO and visible-light photoredox catalysis. The reaction is performed using ammonium persulfate as both the terminal oxidant and nitrogen source.

2018 ◽  
Vol 54 (100) ◽  
pp. 14065-14068 ◽  
Author(s):  
Qiong Yang ◽  
Fengqian Zhao ◽  
Na Zhang ◽  
Mingke Liu ◽  
Huanhuan Hu ◽  
...  

A mild and efficient dynamic kinetic resolution (DKR) of amines was achieved by combining visible-light-induced photoredox catalysis and enzyme catalysis. This dual catalytic system was appropriate for both monoamines and 1,4-diamines.


2017 ◽  
Vol 15 (39) ◽  
pp. 8295-8301 ◽  
Author(s):  
Jyoti Nandi ◽  
John M. Ovian ◽  
Christopher B. Kelly ◽  
Nicholas E. Leadbeater

The merger of oxoammonium cation mediated oxidation with visible-light photoredox catalysis is demonstrated in the oxidative amidation of aldehydes and alcohols.


2018 ◽  
Vol 16 (25) ◽  
pp. 4715-4719 ◽  
Author(s):  
Vincent A. Pistritto ◽  
Joshua M. Paolillo ◽  
Kathryn A. Bisset ◽  
Nicholas E. Leadbeater

The merger of oxoammonium cation mediated oxidation with visible-light photoredox catalysis is demonstrated in the oxidation of α-trifluoromethyl and non-fluorinated alcohols.


RSC Advances ◽  
2015 ◽  
Vol 5 (23) ◽  
pp. 17383-17388 ◽  
Author(s):  
Wei Liu ◽  
Sheng Liu ◽  
Hongqi Xie ◽  
Zhixing Qing ◽  
Jianguo Zeng ◽  
...  

Visible light promoted the oxidation of compounds 1 to amides 2 which were easily transferred to compounds 12.


2019 ◽  
Vol 17 (41) ◽  
pp. 9182-9186 ◽  
Author(s):  
Jyoti Nandi ◽  
Nicholas E. Leadbeater

A mild and efficient route to prepare nitriles from aldehydes by combining photoredox catalysis with oxoammonium cations is reported. The methodology is also extended to the one-pot two-step conversion of alcohols to nitriles.


Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.


Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion


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