Visible light photoredox catalysis: regioselective radical addition of aminoalkyl radicals to 2,3-allenoates

RSC Advances ◽  
2015 ◽  
Vol 5 (68) ◽  
pp. 55290-55294 ◽  
Author(s):  
Xiaojun Dai ◽  
Renjie Mao ◽  
Baochuan Guan ◽  
Xiaoliang Xu ◽  
Xiaonian Li
Keyword(s):  
Visible Light ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Regioselective Addition

Visible-light-mediated regioselective addition of α-aminoalkyl radicals to 2,3-allenoates catalyzed by a photoredox catalyst was developed. The scope and generality of the substrates were broad.

ChemInform Abstract: Visible Light Photoredox Catalysis: Regioselective Radical Addition of Aminoalkyl Radicals to 2,3-Allenoates.

ChemInform ◽  
2015 ◽  
Vol 46 (47) ◽  
pp. no-no
Author(s):  
Xiaojun Dai ◽  
Renjie Mao ◽  
Baochuan Guan ◽  
Xiaoliang Xu ◽  
Xiaonian Li
Keyword(s):  
Visible Light ◽  
Radical Addition ◽  
Photoredox Catalysis

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

2020 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Björn Blomkvist ◽  
Jian-Quan Liu ◽  
Peter Dinér ◽  
...  
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Catalytic Amount ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Acid Radical

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. The mechanism for the developed transformation is discussed and the stereodetermining radical addition step was studied by the DFT calculations.

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acid Derivatives through Photoredox Catalysis

2021 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Elena Vladimirovna Stepanova ◽  
Jian-Quan Liu ◽  
Temerdashev Azamat ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Visible Light ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Radical Addition ◽  
Amino Acid Derivatives ◽  
Photoredox Catalysis

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived N-sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids....

Visible light-induced intermolecular radical addition: facile access to γ-ketoesters from alkyl-bromocarboxylates and enamines

2014 ◽  
Vol 50 (88) ◽  
pp. 13547-13550 ◽  
Author(s):  
Bei Hu ◽  
Haixia Chen ◽  
Yan Liu ◽  
Wuheng Dong ◽  
Kai Ren ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Highly Efficient

A highly efficient addition of alkyl α-bromocarboxylates to enamines by visible light-induced photoredox catalysis is reported.

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

2020 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Björn Blomkvist ◽  
Jian-Quan Liu ◽  
Peter Dinér ◽  
...  
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Catalytic Amount ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Acid Radical

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. The mechanism for the developed transformation is discussed and the stereodetermining radical addition step was studied by the DFT calculations.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

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.

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

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

Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis

2013 ◽  
Vol 15 (9) ◽  
pp. 2136-2139 ◽  
Author(s):  
Yusuke Yasu ◽  
Takashi Koike ◽  
Munetaka Akita
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Visible Light Driven
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