Article
Chemistry, Organic
Hai-Jun Tang, Bin Zhang, Fei Xue, Chao Feng
Summary: An unprecedented approach has been developed for assembling a wide range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers. The key to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and single electron acceptor, enabling a radical-polar crossover manifold.
Article
Chemistry, Organic
Alexis Prieto, Marc Taillefer
Summary: An efficient photoredox system based on decatungstate/disulfide catalysts was developed for the hydrofunctionalization of styrenes. The use of disulfide as a cocatalyst was crucial for enhancing reaction efficiency, allowing for the synthesis of a wide variety of useful building blocks and high-value molecules from simple starting materials, such as amides and unsymmetrical ketones.
Article
Chemistry, Organic
Yang Liu, Simone Battaglioli, Lorenzo Lombardi, Arianna Menichetti, Giovanni Valenti, Marco Montalti, Marco Bandini
Summary: The study documents a visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids, leading to chemo- and regioselective allylic functionalization of styryl compounds, yielding allylic carboxylates. Both intermolecular and intramolecular variants are achieved in high yields, with a proposed mechanistic rationale based on experimental and spectroscopic investigation.
Article
Chemistry, Organic
Jiaxuan Shen, Jincan Li, Meijun Chen, Yimin Chen
Summary: Here, a visible light-induced photocatalytic protocol is reported for the thiolation and pyridylation of styrenes using a thiolate-based EDA complex as a bifunctional reagent. The reaction takes place under mild conditions without the need for a photocatalyst, metal, or external redox agent, and exhibits a broad substrate scope. The protocol can be scaled up to gram-scale, and late-stage functionalization of natural product- and drug-derived complex molecules is also feasible.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Lvyin Zheng, Liuhuan Cai, Xiaoya Zhuo, Lei Deng, Yingying Wu, Beining Yang, Yihan Wang, Wei Guo
Summary: A visible-light-photoredox-catalyzed three-component aminotrifluoromethylation of styrenes with phenylhydrazines and Togni's reagents/fluoroalkyl iodides is reported. This method involves the direct formation of new C-N/C-C bonds and the cleavage of an N-N bond in one pot. It is operationally simple, shows good functional group tolerance, and can be further applied to the late-stage structural modification of bioactive pharmaceuticals for medicinal chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Ramesh Kumar Vishwakarma, Saurabh Kumar, Krishna Nand Singh
Summary: A facile photocatalyzed strategy has been developed for the difunctionalization of styrenes in the presence of CS2 and amines, resulting in the formation of beta-keto dithiocarbamates. Interestingly, in the case of 4-nitrostyrene and 2-vinylpyridine, only 2-arylethylthiocarbamates are formed without the aid of photoredox catalysis/TBHP.
Article
Chemistry, Organic
Yunlong Li, Haibo Liu, Zilong Huang, Yuan He, Bao-Hua Xu, Hongmei Wang, Zhengkun Yu
Summary: Functionalized 1,3-dienes were efficiently accessed through palladium-catalyzed Heck reaction under mild conditions, showcasing tolerance of various functional groups and further transformation potential to highly functionalized trisubstituted furan derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Feng Su, Haoyu Peng, Hui Yin, Chao Luo, Lixia Zhu, Wenzhou Zhong, Liqiu Mao, Dulin Yin
Summary: This study reports a clean and economic strategy to fabricate hydrochar microspheres as the first metal-free biochar potocatalysts from biowaste. The obtained hydrochars exhibit excellent photocatalytic activity and reusability for selective oxidative coupling reactions under visible-light irradiation, showcasing the potential of sustainable biowaste-derived hydrochar materials as low-cost and eco-environmental carbocatalysts for diverse organic transformations.
JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Organic
Zhiwei Wang, Jindong Hao, Yufen Lv, Chengming Qu, Huilan Yue, Wei Wei
Summary: A simple and green visible-light-initiated strategy has been established for the installation of cyano and azido groups through a multi-component reaction. The method allows for the efficient synthesis of diverse organic nitriles and azides without the need for external reagents or catalysts.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Jiale Shi, Tao Yuan, Meifang Zheng, Xinchen Wang
Summary: A protocol utilizing metal-free ceramic BCN for the photocatalytic decarboxylation of carboxylic acids has been developed, demonstrating efficient formation of carbon-centered radicals and carbon-carbon bonds, showing practicality and wide application prospects.
Article
Chemistry, Organic
Shiwei Xia, Linna Wu, Guizhi Zhai, Zechao Wang, Junliang Wu
Summary: Visible-light-promoted CO2 oxidative radical reactions have gained increasing attention in organic synthesis. However, current methods only result in the formation of dimer products from simple organic compounds using CO2 as an oxidant. In this study, we demonstrate a visible-light-promoted CO2 oxidative three-component 1,2-thiosulfonylation of styrenes with sodium sulfinates and thiophenols. The use of CO2 as an oxidant is crucial, and no extra stoichiometric amounts of reductants are required. Our photocatalytic strategy enables the conversion of CO2 to fuels CO and CH4, offering a new approach to combine CO2-to-fuel conversion and organic synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Hao Wang, Qi Wu, Jian-Dong Zhang, Hai-Yan Li, Hong-Xi Li
Summary: A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed, leading to the efficient and selective formation of 2-aryl benzothiazoles. This photocyclization is highly tolerant to various functional groups, suitable for the synthesis of 2-alkyl benzothiazoles, and easy to scale up for gram-scale reactions.
Article
Chemistry, Organic
Lu Zhang, Shuai Liu, Mingming Ma, Yuncheng Shen, Pin Gao, Li-Na Guo, Xin-Hua Duan
Summary: This study describes metal-free, visible light-induced difunctionalizations of alpha-CF3 styrenes with aryl diazonium salts and various hetero nucleophiles. The concise protocol provides easy access to the alpha-CF3 tertiary alkyl ethers, alcohol, and fluorides with good yields and excellent functional group tolerance. Additionally, a radical-polar crossover coupling pathway is proposed for the C-O bond formation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Dan Louvel, Aida Chelagha, Jean Rouillon, Pierre-Adrien Payard, Lhoussain Khrouz, Cyrille Monnereau, Anis Tlili
Summary: The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported in this study. The reaction using organo-photoredox conditions allows aryl diazonium salts to react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. Experimental techniques such as fluorescence, NMR, and EPR spectroscopy, as well as DFT calculations, were used to shed light on the reaction mechanism.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Xiaodi Shi, Yunpeng Cao, Yuxiu Liu, Kaikai Niu, Hongjian Song, Jingjing Zhang, Qingmin Wang
Summary: Direct functionalization of C(sp(3))-H bonds is a useful method for obtaining a variety of heteroarene derivatives. However, its application is limited by the need for catalysts or oxidants. In this study, a mild and eco-friendly photochemical protocol was developed for decarbonylative C-H alkylation reactions using quinoxalin-2(1H)-ones and aliphatic aldehydes with air as the oxidant at room temperature. These catalyst- and oxidant-free reactions exhibited good functional group tolerance and a wide substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Chitrakar Ravi, N. Naresh Kumar Reddy, Venkatanarayana Pappula, Supravat Samanta, Subbarayappa Adimurthy
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Chitrakar Ravi, Abhisek Joshi, Subbarayappa Adimurthy
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Supravat Samanta, Chitrakar Ravi, Sadu Nageswara Rao, Abhisek Joshi, Subbarayappa Adimurthy
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Venkatanarayana Pappula, Chitrakar Ravi, Supravat Samanta, Subbarayappa Adimurthy
Article
Chemistry, Organic
Deepa Rawat, Chitrakar Ravi, Abhisek Joshi, Eringathodi Suresh, Kalyanashis Jana, Bishwajit Ganguly, Subbarayappa Adimurthy
Article
Chemistry, Multidisciplinary
Rahul Kumar, Chitrakar Ravi, Abhisek Joshi, Rashmi Semwal, Subbarayappa Adimurthy
Article
Chemistry, Organic
Rahul Kumar, Abhisek Joshi, Deepa Rawat, Subbarayappa Adimurthy
Summary: An expeditious approach for the synthesis of thiazolidin-2-imines and 1,3-thiazinan-2-imines through three-components coupling under metal-free conditions has been described. The advantages of this protocol include metal-free conditions, broad substrate scope, functional group tolerance, and applicability at gram scale synthesis.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Gaurav Badhani, Abhisek Joshi, Subbarayappa Adimurthy
Summary: The study introduces a metal-free method for the synthesis of imines using oxygen as the terminal oxidant, achieving oxidative coupling of amines and alcohols to form C-N, C-S, and C-C bonds. This method features mild reaction conditions and broad applicability.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ishani Borthakur, Milan Maji, Abhisek Joshi, Sabuj Kundu
Summary: This study demonstrates an efficient protocol for the reductive alkylation of azides/nitro compounds using a borrowing hydrogen (BH) method, resulting in selective mono- and dialkylated amines under mild and solvent-free conditions. Mechanistic studies reveal the involvement of Ir(III)-H as the active intermediate, with the breaking of the C-H bond of alcohol potentially being the rate-limiting step. A high TON of around 5600 was achieved with a proposed metal-ligand cooperative mechanism based on kinetic studies and control experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Abhisek Joshi, Rashmi Semwal, Subbarayappa Adimurthy
Summary: This study describes the ruthenium-catalyzed efficient and selective C-H alkenylation of pyridotriazoles with acrylates, where the combination of metals (Ru and Fe) plays a crucial role in achieving quantitative yields of the desired products. The reaction is proposed to involve the formation of a ruthenium cyclometalated intermediate.
Article
Chemistry, Multidisciplinary
Rashmi Semwal, Abhisek Joshi, Rahul Kumar, Subbarayappa Adimurthy
NEW JOURNAL OF CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Abhisek Joshi, Rashmi Semwal, Eringathodi Suresh, Subbarayappa Adimurthy
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Abhisek Joshi, Rahul Kumar, Rashmi Semwal, Deepa Rawat, Subbarayappa Adimurthy
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
