Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis

2020 ◽  
Vol 142 (20) ◽  
pp. 9493-9500 ◽  
Author(s):  
Eric W. Webb ◽  
John B. Park ◽  
Erin L. Cole ◽  
David J. Donnelly ◽  
Samuel J. Bonacorsi ◽  
...  
Keyword(s):  
Photoredox Catalysis ◽  
Active Esters ◽  
Redox Active

Photoredox catalysis enabled alkylation of alkenyl carboxylic acids with N-(acyloxy)phthalimide via dual decarboxylation

2017 ◽  
Vol 53 (77) ◽  
pp. 10719-10722 ◽  
Author(s):  
Kun Xu ◽  
Zhoumei Tan ◽  
Haonan Zhang ◽  
Juanli Liu ◽  
Sheng Zhang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Photoredox Catalysis ◽  
Active Esters ◽  
Redox Active

A ruthenium based photoredox catalyst in combination with DBACO efficiently catalyzed dual decarboxylative couplings between alkenyl carboxylic acids and redox active esters.

Recent Advances in Photoredox Catalysis Enabled Functionalization of α-Amino Acids and Peptides: Concepts, Strategies and Mechanisms

Synthesis ◽  
2019 ◽  
Vol 51 (14) ◽  
pp. 2759-2791 ◽  
Author(s):  
Jian-Quan Liu ◽  
Andrey Shatskiy ◽  
Bryan S. Matsuura ◽  
Markus D. Kärkäs
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Hypervalent Iodine ◽  
Amino Acid Residues ◽  
Photoredox Catalysis ◽  
Metal Catalysis ◽  
Specific Amino Acid ◽  
Recent Advances ◽  
Redox Active ◽  
Decarboxylative Coupling

The selective modification of α-amino acids and peptides constitutes a pivotal arena for accessing new peptide-based materials and therapeutics. In recent years, visible light photoredox catalysis has appeared as a powerful platform for the activation of small molecules via single-electron transfer events, allowing previously inaccessible reaction pathways to be explored. This review outlines the recent advances, mechanistic underpinnings, and opportunities of applying photoredox catalysis to the expansion of the synthetic repertoire for the modification of specific amino acid residues.1 Introduction2 Visible-Light-Mediated Functionalization of α-Amino Acids2.1 Decarboxylative Functionalization Involving Redox-Active Esters2.2 Direct Decarboxylative Coupling Strategies2.3 Hypervalent Iodine Reagents2.4 Dual Photoredox and Transition-Metal Catalysis2.5 Amination and Deamination Strategies3 Photoinduced Peptide Diversification3.1 Gese-Type Bioconjugation Methods3.2 Peptide Macrocyclization through Photoredox Catalysis3.3 Biomolecule Conjugation through Arylation3.4 C–H Functionalization Manifolds4 Conclusions and Outlook

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
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