Article
Chemistry, Organic
Yuki Yoshida, Haruka Takeuchi, Kohei Nakagawa, Toshiki Fujii, Norihito Arichi, Shinya Oishi, Hiroaki Ohno, Shinsuke Inuki
Summary: In this study, it was found that simple biphenyl substrates derived from amino acids can participate in a radical cascade reaction under visible light irradiation in the presence of [Ir{dF(CF3)ppy}(2)(dtbpy)]PF6, enabling the direct construction of bicyclo[2.2.2]octene structures. Isotopic labeling experiments suggested that intramolecular hydrogen atom transfer is involved in the cascade processes.
Article
Chemistry, Organic
Tathagata Choudhuri, Suvam Paul, Sourav Das, Devendra Deo Pathak, Avik Kumar Bagdi
Summary: An efficient visible-light-induced methodology using erythrosine B as the photocatalyst has been developed for the regioselective selenylation of pyrazolo[1,5-a]pyrimidine derivatives. The methodology has also been demonstrated to be efficient for selenylation of different electron-rich heterocycles. The use of erythrosine B as the photocatalyst, along with the simplicity of the procedure and the eco-friendly energy, oxidant, and solvent employed, are attractive characteristics of this methodology.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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)
Article
Chemistry, Organic
Xiao-Di Su, Bei-Bei Zhang, Qiang Liu, Jin-Tang Cheng, Zhi-Xiang Wang, Xiang-Yu Chen
Summary: Enamides are useful precursors for the synthesis of bioactive compounds. A simple alternative method for their alkylation has been proposed in this study, which involves using visible light to irradiate a mixture of N-hydroxyphthalimide esters and enamides without the need for additives. The reaction is based on the photoactivation of a pi-pi stacking EDA complex between the substrates.
Article
Chemistry, Organic
Srilaxmi M. Patel, Ermiya P. Prasad, Manickam Bakthadoss, Duddu S. Sharada
Summary: This study demonstrates a visible-light-mediated metal-free organic-dye-catalyzed dehydrogenative N-insertion for the synthesis of highly substituted imidazoles and dihydroisoquinoline-based imidazole derivatives via functionalization of C(sp(3))-H and C-(sp(2))-H bonds. The sustainable and convenient metal-free azidation/C-H aminative cyclization approach without stoichiometric oxidants involves a rare photoinduced iminyl radical as a key intermediate for the N insertion.
Article
Chemistry, Multidisciplinary
Hao Guo, Huahao Wang, Hongyi Zhao, Dongfeng Zhang
Summary: This article reports a visible light-induced diastereoselective synthesis of 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-diones using 2H-azirines and maleimides in the presence of an organic photocatalyst. The method is efficient, environmentally friendly, and shows good tolerance towards functional groups and substrates. Applications of the cycloaddition products were demonstrated through simple synthetic transformations.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Wenwen Cui, Xufeng Li, Guoju Guo, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: In this study, a copper-catalyzed blue-light-induced free radical ring-opening reaction of sulfonium salts with dichalcogenides was developed. The method utilizes an inexpensive copper catalyst and has a broad substrate scope, allowing for the high-yield synthesis of alkyl chalcogenides. This reaction presents a novel ring-opening model for sulfonium salts, breaking the limitation of only nucleophilic ring-opening reactions to form C-heteroatom and C-C bonds.
Article
Chemistry, Multidisciplinary
Yanmin Guo, Rong Chang, Zhen Fu, Cong-Ying Zhou, Zhen Guo
Summary: This study presents a visible-light-induced dehydrogenative [4+2] annulation of benzothioamides and alkynes using the metal-free heterogeneous photocatalyst graphitic carbon nitride (g-C3N4). The reaction proceeds smoothly under mild aerobic conditions and gives a variety of isothiochromenes in good yields. Detailed mechanistic studies reveal that g-C3N4 promotes the formation of a sulfur-centered radical under visible-light irradiation through a single electron transfer process.
Review
Chemistry, Organic
Sumit Ghosh, Pranjal Pyne, Anogh Ghosh, Swagata Choudhury, Alakananda Hajra
Summary: Photoredox catalysis has rapidly evolved in synthetic organic chemistry, while cascade reactions have emerged as a cutting-edge research area for complex molecular architectures. The merger of photocatalysis with cascade synthesis presents a synthetic paradigm with immense potential. This comprehensive review summarizes the achievements and highlights of visible-light-induced cascade reactions up to October 2022 with literature coverage.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Babita Yadav, Arvind Kumar Yadav, Vishnu Prabhakar Srivastava, Santosh K. Srivastava
Summary: A convenient and efficient method for the synthesis of 2-amino-1,3,4-oxadiazoles from N-acyl thiosemicarbazides using aerobic visible light photoredox catalysis is reported. This protocol demonstrates the first example of oxidative cyclodesulfurization of N-acyl thiosemicarbazides using visible light and air as inexpensive, readily available, non-toxic, and sustainable reagents.
TETRAHEDRON LETTERS
(2023)
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, Organic
Cong Ye, Bao-Gui Cai, Juan Lu, Xiao Cheng, Lei Li, Zhong-Wen Pan, Jun Xuan
Summary: The method uses a blue-light LED to promote the coupling of aryl diazoacetates with sulfur ylides, featuring mild conditions, good functional group tolerance, and a broad substrate scope. Under optimal reaction conditions, a variety of trisubstituted olefins can be synthesized and further transformed into other important biologically active heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sameer R. Sonavane, Santosh B. Mhaske
Summary: Direct visible light-mediated intramolecular decarboxylative C-H functionalization of Csp(2)-H bond adjacent to the nitrogen of a heteroarene has been achieved by iridium-catalyzed photodecarboxylative radical cyclization. This method offers rapid entry to the synthesis of quinazolinone scaffolds from easily accessible starting materials. The utility of this unique Csp(3)-Csp(2) bond forming reaction has been demonstrated in the syntheses of Circumdatin, Sclerotigenine, and Benzomalvin A class of quinazolinone natural products and their congeners. The present work represents an interesting example of use of memory of chirality in decarboxylative C-C bond forming enantioselective photoredox reaction.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Yameng Wan, Qingfeng Liu, Hao Wu, Zhiguo Zhang, Guisheng Zhang
Summary: In this study, 2,11-dimethoxyldipyridopurinone (DP4) is reported as a potent reducing visible-light photocatalyst for three organic transformations. The study demonstrates the potential of dipyridopurinone derivatives as a new class of metal-free visible-light photocatalysts for various organic transformations.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jiaqing Lu, Yan Yao, Liubo Li, Niankai Fu
Summary: The direct decarboxylative alkenylation of widely available aliphatic carboxylic acids with vinyl halides has been achieved using Ce/Ni dual transition metal electrocatalysis. This reaction allows for the synthesis of alkenes with all substitution patterns and has a broad scope with respect to both coupling partners. The reaction can readily utilize simple primary alkyl carboxylic acids as carbon-centered radical precursors. Mechanistic studies have been conducted to understand the key intermediates and pathway of the reaction using controlled experiments and cyclic voltammetry data.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
