scholarly journals Nickel-Catalyzed Decarboxylative Coupling of Redox-Active Esters with Aliphatic Aldehydes

2021 ◽  
Author(s):  
Jichao Xiao ◽  
Zhenning Li ◽  
John Montgomery
Keyword(s):  
Aliphatic Aldehydes ◽  
Active Esters ◽  
Redox Active ◽  
Decarboxylative Coupling

scholarly journals Nickel-Catalyzed Decarboxylative Coupling of Redox-Active Esters with Aliphatic Aldehydes

2021 ◽  
Author(s):  
Jichao Xiao ◽  
Zhenning Li ◽  
John Montgomery
Keyword(s):  
Catalytic Reactions ◽  
Reductive Coupling ◽  
Nickel Catalysis ◽  
Mechanistic Studies ◽  
Radical Chain ◽  
Aliphatic Aldehydes ◽  
Active Esters ◽  
Redox Active ◽  
Decarboxylative Coupling ◽  
Nucleophilic Reagents

The addition of alkyl fragments to aliphatic aldehydes is a highly desirable transformation for fragment couplings, yet existing methods come with operational challenges related to the basicity and instability of the nucleophilic reagents commonly employed. We report herein that nickel catalysis using a readily available bioxazoline (BiOx) ligand can catalyze the reductive coupling of redox-active esters with aliphatic aldehydes using zinc metal as the reducing agent to deliver silyl-protected secondary alcohols. This protocol is operationally simple, proceeds under mild conditions, and tolerates a variety of functional groups. Initial mechanistic studies suggest a radical chain pathway. Additionally, alkyl tosylates and epoxides are suitable alkyl precursors to this transformation providing a versatile suite of catalytic reactions for the functionalization of aliphatic aldehydes.

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.

Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide

Science ◽  
2019 ◽  
Vol 363 (6434) ◽  
pp. 1429-1434 ◽  
Author(s):  
Ming-Chen Fu ◽  
Rui Shang ◽  
Bin Zhao ◽  
Bing Wang ◽  
Yao Fu
Keyword(s):  
Large Scale ◽  
Sodium Iodide ◽  
Organic Dyes ◽  
Industrial Processes ◽  
Enol Ethers ◽  
Light Emitting ◽  
Silyl Enol Ethers ◽  
Redox Active ◽  
Decarboxylative Coupling ◽  
The Cost

Most photoredox catalysts in current use are precious metal complexes or synthetically elaborate organic dyes, the cost of which can impede their application for large-scale industrial processes. We found that a combination of triphenylphosphine and sodium iodide under 456-nanometer irradiation by blue light–emitting diodes can catalyze the alkylation of silyl enol ethers by decarboxylative coupling with redox-active esters in the absence of transition metals. Deaminative alkylation using Katritzky’s N-alkylpyridinium salts and trifluoromethylation using Togni’s reagent are also demonstrated. Moreover, the phosphine/iodide-based photoredox system catalyzes Minisci-type alkylation of N-heterocycles and can operate in tandem with chiral phosphoric acids to achieve high enantioselectivity in this reaction.

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
Sign in / Sign up

Export Citation Format

Share Document