Decarboxylative sulfenylation of amino acids via metallaphotoredox catalysis

2019 ◽  
Vol 6 (18) ◽  
pp. 3224-3227 ◽  
Author(s):  
Lidan Wei ◽  
Chengjuan Wu ◽  
Chen-Ho Tung ◽  
Wenguang Wang ◽  
Zhenghu Xu
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Mild Conditions ◽  
Cooperative Catalysis

A nickel/visible light photoredox co-catalyzed decarboxylative thiolation reaction of carboxylic acids has been developed. This odorless sulfenylation reaction proceeded well via a nickel/photoredox cooperative catalysis pathway under very mild conditions.

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1572-1577 ◽  
Author(s):  
Hua Fu ◽  
Min Jiang ◽  
Haijun Yang ◽  
Yunhe Jin ◽  
Lunyu Ou
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Functional Groups ◽  
High Efficiency ◽  
Aromatic Carboxylic Acids ◽  
Mild Conditions ◽  
Aryl Iodides

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids

2019 ◽  
Vol 55 (7) ◽  
pp. 933-936 ◽  
Author(s):  
Thomas Duhamel ◽  
Kilian Muñiz
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Molecular Iodine ◽  
Organic Dye ◽  
Photoredox Catalysis ◽  
Cooperative Catalysis

C–H lactonization is enabled by visible light-promoted cooperative catalysis combining molecular iodine and an organic dye.

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.

Visible-Light-Mediated Synthesis of Amides from Carboxylic Acids and Amine Boranes

2021 ◽  
Author(s):  
Yuqi Miao ◽  
Jiaxin Kang ◽  
Yan-Na Ma ◽  
Xuenian Chen
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Scale Up ◽  
Mild Conditions ◽  
Amine Boranes

Herein, a mild photocatalytic deoxygenative amidation protocol using readily available amine borane and carboxylic acids was uncovered. This approach features mild conditions, moderate to good yields, easy scale-up, and up...

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 Mechanically induced solvent-free esterification method at room temperature

RSC Advances ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 5080-5085
Author(s):  
Lei Zheng ◽  
Chen Sun ◽  
Wenhao Xu ◽  
Alexandr V. Dushkin ◽  
Nikolay Polyakov ◽  
...  
Keyword(s):  
Natural Products ◽  
Carboxylic Acids ◽  
Late Stage ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Solvent Free ◽  
Mild Conditions

We have developed I2/KH2PO2 and KI/P(OEt)3 strategy syntheses of esters from carboxylic acids and alcohols through different reaction mechanisms. The advantages of present protocol: mild conditions and late-stage diversification of natural products.

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

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