Visible‐Light‐Mediated Dual Decarboxylative Coupling of Redox‐Active Esters with α,β‐Unsaturated Carboxylic Acids

2017 ◽  
Vol 23 (43) ◽  
pp. 10259-10263 ◽  
Author(s):  
Jin‐Jiang Zhang ◽  
Jun‐Cheng Yang ◽  
Li‐Na Guo ◽  
Xin‐Hua Duan
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Active Esters ◽  
Redox Active ◽  
Decarboxylative Coupling ◽  
Unsaturated Carboxylic Acids

Visible-Light-Induced Copper-Catalyzed Decarboxylative Coupling of Redox-Active Esters with N-Heteroarenes

2019 ◽  
Vol 21 (14) ◽  
pp. 5728-5732 ◽  
Author(s):  
Xue-Li Lyu ◽  
Shi-Sheng Huang ◽  
Hong-Jian Song ◽  
Yu-Xiu Liu ◽  
Qing-Min Wang
Keyword(s):  
Visible Light ◽  
Active Esters ◽  
Redox Active ◽  
Decarboxylative Coupling

Visible-light induced decarboxylative coupling of redox-active esters with disulfides to construct C–S bonds

2020 ◽  
Vol 56 (30) ◽  
pp. 4164-4167 ◽  
Author(s):  
Zhiwei Xiao ◽  
Lu Wang ◽  
Junjie Wei ◽  
Chongzhao Ran ◽  
Steven H. Liang ◽  
...  
Keyword(s):  
Visible Light ◽  
Active Esters ◽  
Redox Active ◽  
Decarboxylative Coupling ◽  
Novel Method

A novel method has been established for the construction of C–S bonds using redox-active esters with disulfides in the presence of Ru-photoredox catalyst.

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

Cu-Photoredox-catalyzed C(sp)–C(sp3) coupling of redox-active esters with terminal alkynes

2020 ◽  
Vol 18 (23) ◽  
pp. 4479-4483
Author(s):  
Yajing Zhang ◽  
Dayong Zhang
Keyword(s):  
Carboxylic Acids ◽  
Mild Condition ◽  
Terminal Alkynes ◽  
Active Esters ◽  
Redox Active ◽  
Esters Of Carboxylic Acids

Under mild condition, redox-active esters of carboxylic acids reacted with aryl and alkyl substituted alkynes in good yields. A copper-acetylid-ligand is a key intermediate for constructing C(sp)–C(sp3) bond.

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

2020 ◽  
Author(s):  
Eric Webb ◽  
John Park ◽  
Erin L. Cole ◽  
David J. Donnelly ◽  
Samuel Bonacorsi, Jr. ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Active Esters ◽  
Mild Conditions ◽  
Redox Active ◽  
Active Ester ◽  
Electron Transfers ◽  
Ester Substrate ◽  
Nucleophilic Fluorination

<p>We report a redox-neutral method for nucleophilic fluorination of N-hydroxyphthalimide esters using an Ir photocatalyst under visible light irradiation. The method provides access to a broad range of aliphatic fluorides, including primary, secondary, and tertiary benzylic fluorides as well as unactivated tertiary fluorides, that are typically inaccessible by nucleophilic fluorination due to competing elimination. In addition, we show that the decarboxylative fluorination conditions are readily adapted to radiofluorination with [<sup>18</sup>F]KF. We propose that the reactions proceed by two electron transfers between the Ir catalyst and redox-active ester substrate to afford a carbocation intermediate that undergoes subsequent trapping by fluoride. Examples of trapping with O- and C-centered nucleophiles and deoxyfluorination via N-hydroxyphthalimidoyl oxalates are also presented, suggesting that this approach may offer a general blueprint for affecting redox-neutral SN1 substitutions under mild conditions.</p>

Quaternary Centers via Ni-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and Aryl Zinc Reagents

2018 ◽  
Author(s):  
Phil Baran ◽  
Pavel Mykhailiuk ◽  
haolin zhang ◽  
Rohan R. Merchant ◽  
Courtney A. Smith ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Cross Coupling ◽  
Simple Method ◽  
Quaternary Centers ◽  
Active Esters ◽  
Redox Active ◽  
The Cross

<div> <div> <div> <p>This work bridges a gap in the cross-coupling of aliphatic redox-active esters with aryl zinc reagents. Previously limited to primary, secondary and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using Ni-catalysis. The scope of this operationally simple method is broad and can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers. </p> </div> </div> </div>

Visible-light-induced iodine anion catalyzed decarboxylative/ deaminative C-H alkylation of enamides

2021 ◽  
Author(s):  
Jia-Xin Wang ◽  
Ya-Ting Wang ◽  
Hao Zhang ◽  
Ming-Chen Fu
Keyword(s):  
Amino Acid ◽  
Visible Light ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Active Esters ◽  
Cross Coupling Reactions ◽  
Redox Active ◽  
Iodine Anion

A visible-light-induced iodine anion catalyzed C-H stereoselective alkylation of enamides has been developed. Redox-active esters and Katritzky salts of the amino acid are amenable for decarboxylative/deaminative cross-coupling reactions, delivering various...

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.

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