Review
Chemistry, Applied
Jitender Singh, Anuj Sharma
Summary: Functionalized oxindoles are important heterocyclic structures found in many natural products and are key intermediates in drug synthesis. Visible light mediated methodologies for the synthesis of oxindoles have received significant attention and show promise for future applications.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Yu Zhang, Jiahui Qian, Miao Wang, Yahao Huang, Peng Hu
Summary: An efficient and low-cost protocol for the direct decarboxylative fluorination of aliphatic carboxylic acids catalyzed by iron salts under visible light is presented. This new method is highly efficient and scalable, and mechanistic studies have revealed the generation process of the key step.
Article
Chemistry, Organic
Penglei Cui, Sida Li, Xianjin Wang, Ming Li, Chun Wang, Lipeng Wu
Summary: In this study, the catalytic deaminative alkylation of phosphine compounds was achieved using visible-light photoredox catalysis. The use of Eosin Y as the photoredox catalyst and visible light significantly promoted the reaction, leading to the successful synthesis of a series of unsymmetrical tertiary phosphines, including compounds with three different substituents that are otherwise difficult to obtain.
Article
Chemistry, Multidisciplinary
Quan-Qing Zhao, Julia Rehbein, Oliver Reiser
Summary: This study presents a visible-light-driven dearomatization reaction of unactivated arenes, enabling efficient synthesis of spiro-1,4-cyclohexadienes. Calculations indicate that the overall process is thermoneutral, highlighting the potential of light-driven processes in developing sustainable transformations that defy thermodynamic requirements.
Article
Chemistry, Multidisciplinary
Dario Filippini, Mattia Silvi
Summary: The study presents a visible-light-mediated and transition metal-free olefination process using a defined alkene geometry to cross-couple complex molecular scaffolds containing carboxylic acids and aldehydes. By merging the Wittig reaction and photoredox catalysis, it enables rapid structural diversification of bioactive molecules and natural products with high functional group tolerance and the formation of a new alkene functional group with programmable E-Z stereochemistry.
Article
Chemistry, Multidisciplinary
Wenzhao Zhang, Sanzhong Luo
Summary: A zirconium-catalyzed de Mayo reaction under visible light conditions was developed without the need for external photosensitizers and additives.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Jia-Hao Shen, Min Shi, Yin Wei
Summary: The combination of visible light photocatalysis and organocatalysis has been widely used in various reactions in recent years. The synergy between visible light photocatalysis and organocatalysis has led to significant progress in modern chemical synthesis. In these dual catalytic systems, photocatalysts or photosensitizers absorb visible light to activate unreactive substrates through electron or energy transfer mechanisms, while organocatalysts are used to control the reactivities of other substrates. This review primarily focuses on the recent advancements in cooperative catalysis by the combination of organocatalysis and photocatalysis in organic synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Shuai Yao, Xiaowei Zhao, Xu Ban, Tianju Shao, Yanli Yin, Weigao Hu, Zhiyong Jiang
Summary: Radical-based functionalization-oriented construction (FoC) is a powerful method for the direct synthesis of imine-containing azaarene derivatives. In this study, a novel FoC method was developed for the direct synthesis of highly functionalized pyrroles. This method involves the reaction of α-amino acids with easily accessible α/β-azaarene-substituted enones under visible light irradiation and with the presence of p-toluenesulfonic acid as an additive.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Sriram Vijayakrishnan, John W. Ward, Andrew I. Cooper
Summary: In this study, a novel photocatalyst CTF-2 was discovered for decarboxylative conjugate addition under visible-light irradiation. CTF-2 showed the ability to couple with various other reactions and can be prepared on a large scale with recyclability.
Article
Chemistry, Organic
Chang Xu, Fang-Qi Shen, Gaofeng Feng, Jian Jin
Summary: A novel visible-light-induced alpha-amino C-H bond arylation protocol has been discovered, enabled by electron donor-acceptor complexes. This method does not require a photoredox catalyst, transition metal, oxidant, or exclusion of oxygen or moisture. High yields of arylated amines were obtained by directly irradiating a mixture of tertiary amines and benzonitriles with visible light in the presence of Cs2CO3 in N,N-diethylethanamide.
Article
Chemistry, Physical
Sriram Vijayakrishnan, John W. Ward, Andrew I. Cooper
Summary: Photoredox catalysis is an important development in organic synthesis, but the current use of homogeneous metal complexes or organic dyes raises issues of cost, recyclability, and waste production. In this study, a covalent triazine framework photocatalyst (CTF-2) was discovered, which enables decarboxylative conjugate addition of carboxylic acids under visible-light irradiation. CTF-2 can be prepared on a large scale and recycled without loss of catalytic efficiency.
Article
Chemistry, Organic
Bao-Gui Cai, Qian Li, Qiong Zhang, Lei Li, Jun Xuan
Summary: An efficient method for synthesizing trisubstituted hydroxylamines has been developed using beta-keto ester, 2-nitrosopyridine, and aryldiazoacetates. This multicomponent reaction can easily produce two different kinds of trisubstituted hydroxylamines by simply changing the reaction media.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Chenguang Liu, Xiaoyi Cui, Wei Chen, Xiaoqiang Ma, Kristala J. Prather, Kang Zhou, Jie Wu
Summary: Combining complementary bioprocessing and chemical transformations can expand the chemical space of natural products for drug discovery. In this study, genetically engineered Escherichia coli fermentation and metal-free photocatalysis were used to synthesize various compounds. The results demonstrate that this combination method is not only efficient, but also environmentally friendly.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Qiupeng Peng, Achyut Ranjan Gogoi, Osvaldo Gutierrez, Angel Renteria-Gomez, Karl A. Scheidt
Summary: This article reports a divergent process for the synthesis of α-hydroxy/amino ketones or β-keto-phosphonates through a light-induced coupling of activated carboxylic acids and alcohols/amines via single-electron chemistry. This process enables new carbon-carbon bond formation using a phosphorous linchpin strategy.
Article
Chemistry, Multidisciplinary
Kathiravan Murugesan, Karsten Donabauer, Burkhard Konig
Summary: The study demonstrates the use of the commercially available organic dye TPP for the photocatalytic conversion of methylarenes to aryl nitriles, providing a wide range of cyanobenzenes under metal- and cyanide-free conditions. The presented synthetic protocol is applicable for gram-scale reactions and includes detailed mechanistic investigations supporting the proposed catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
