Article
Chemistry, Organic
Kshitiz Verma, Manmath Mishra, Prabhat Kumar Maharana, Hemanga Bhattacharyya, Sharajit Saha, Tharmalingam Punniyamurthy
Summary: A Sc(III)-catalyzed domino C-C and C-N bond formation of N-sulfonyl aziridines with quinones has been achieved, leading to the synthesis of functionalized indolines at a moderate temperature. The key practical features of this study include the umpolung reactivity of aziridines, radical pathway, mild reaction conditions, substrate scope, and the coupling of drug molecules in a postsynthetic application.
Article
Chemistry, Organic
Xiang Li, Danlu Li, Xiaofei Zhang
Summary: A Ru(ii)-catalyzed C-H bond activation/annulation reaction of N-iminopyridinium ylides with sulfoxonium ylides has been developed for the synthesis of diverse functionalized isocoumarin derivatives. This method shows broad substrate scope, excellent functional group tolerance, simple operation, and silver salt-free conditions. Furthermore, the utility of this method is demonstrated by the alkenylation of the product and efficient synthesis of biologically active thunberginol A.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Chun-Ting He, Xiao-Li Han, Yan-Xue Zhang, Zhen-Ting Du, Chang-Mei Si, Bang-Guo Wei
Summary: An efficient method has been developed to access functionalized (2,3-dihydroisoxazol-4-yl) ketones by reacting nitrones with ynones or terminal ynones in a one-pot fashion, resulting in moderate to good yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Ali Wang, Peizhuo Lv, Yuanhong Liu
Summary: A five-membered N-O heterocycle, 4,5-dihydro-1,2,4-oxadiazole, is discovered to act as a single nitrogen atom transfer reagent through the elimination reaction of a ketone/aldehyde and a nitrile. This reagent is successfully used in the synthesis of isoxazoles from ynones promoted by Sc(OTf)(3) or through Au(I)/Sc(OTf)(3) synergistic catalysis. The efficiency of this protocol is also demonstrated by its application in modifying structurally complex natural products and pharmaceuticals.
Article
Chemistry, Organic
Chao Xia, Dongchao Wang, Haiming Guo
Summary: Efficient alkylation of purines with ortho-hydroxybenzyl alcohols under mild condition has been achieved by Sc(OTf)(3) catalysis, leading to the formation of various acyclic nucleoside analogs with excellent yields of up to 96% and maintained yields as reactions were scaled up.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Peter-Yong Wang, Itai Massad, Ilan Marek
Summary: The facile and modular access to stereodefined disubstituted aldehyde-derived silyl enol ethers allowed for their successful application in a stereoselective aldol reaction, resulting in excellent yields and diastereomeric ratios. The counter-intuitive stereochemical behavior of this Mukaiyama-aldol reaction is explained by a non-classical open transition state.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Sabera Sultana, Peter Yuosef M. Rubio, Hari Datta Khanal, Yong Rok Lee
Summary: This study describes the Sc(OTf)(3)/BF3 center dot OEt2-catalyzed annulation of 3-formylchromones with functionalized alkenes, providing a direct synthetic route to 2-hydroxybenzophenones. The reaction exhibits excellent regio- and chemoselectivities, suitable for late-stage functionalization. Additionally, it proceeds via [3 + 3] and [4 + 2] cycloaddition processes, tolerating various functional groups found in natural terpenes and steroids.
Article
Chemistry, Organic
Mokhamatam Sudheer, Chinthu Joginarayana Rao, Venkateswara Rao Battula
Summary: The regioselective enone synthesis from intermolecular coupling of aldehydes and alkynes has been developed using triflic acid as the catalyst. This reaction is efficient, effective, simple and mild, with diverse substrate scope. Both aryl and aliphatic aldehydes can smoothly participate in the reaction and exclusively provide trans product.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jianwei Xie, Muhammad Suleman, Ke Zhang, Ping Lu, Yanguang Wang
Summary: In this study, an unexpected cascade ring expansion/annulation reaction was reported between 4-diazo-1,4-dihydroisoquinolin-3-ones and a variety of isatin derivatives in the presence of Sc(OTf)3 catalyst. Novel indolobenzazepinones were synthesized in good to excellent yields by excluding nitrogen and carbon dioxide gases. This method is characterized by high bond-forming efficiency, a novel reaction mechanism, readily available starting materials, commercially available cheap catalyst, broad substrate scope, and mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Daniel S. Brandes, Jonathan A. Ellman
Summary: Sequential multicomponent C-H bond addition is a powerful approach for the rapid generation of complex molecules. This approach involves adding C-H bonds across pi-bonds or pi-bond isosteres and coupling them with another type of functionality to form two sigma-bonds in a single reaction sequence. These atom-economical reactions transform ubiquitous C-H bonds into more complex structures with precise control over regiochemical and stereochemical properties. The development of these reactions has revealed surprising connectivities and diverse mechanisms. The vast number of possible coupling partners offers significant opportunities for the discovery of new sequential C-H bond addition reactions.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Peng Yang, Qiang Wang, Bing-Hui Cui, Xiao-Dong Zhang, Hang Liu, Yue-Yuan Zhang, Jia-Liang Liu, Wen-Yu Huang, Ren-Xiao Liang, Yi-Xia Jia
Summary: This study developed a cobalt-catalyzed enantioselective [3 + 2] annulation of N-heteroarenes with alkynes, providing a straightforward access to a variety of N-spiroheterocyclic molecules with excellent enantioselectivities.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo
Summary: A formal [3 + 3] cyclization reaction has been developed for the synthesis of 1,3,4-oxadiazinanes with generally high yields (up to 96%). The reaction, catalyzed by Sc(OTf)(3), has a broad substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and dipolar quinones was found to be essential for enabling this reaction.
Article
Chemistry, Multidisciplinary
Shanshan Liu, Xianying Zhou, Lin-Yu Jiao, Chao Li, Zheng Wang
Summary: A mild and catalyst-free sunlight induced protocol for the remote meta bromination of electron-deficient indoles is described for the first time. Herein, N-bromosaccharin is activated by sunlight irradiation. Alternately, a synergistic activation model (Sc(OTf)(3)/HFIP) has also been developed for the activation of haloniums, complementary to the light induced strategy. In addition, the cascade C6-H bromination and benzylic C-H oxidation under photocatalytic conditions was also discussed. High regio-and chem-selectivity, mild reaction conditions, and scalability demonstrate great potential of the developed methods in practical applications and further functionalization.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Yingkun Yan, Min Li, Min Liu, Min Huang, Lianyi Cao, Wenzhe Li, Xiaomei Zhang
Summary: Isoxazolines are important for the development of synthetic methodology and pharmaceutics. In this study, a new method using Sc(OTf) catalyst for the dearomative [3 + 2] annulation of 5-aminoisoxazoles with quinone imine ketals (QIKs) and quinone monoacetals (QMAs) was reported. This method allows for the synthesis of fusion compounds of indolines and 2,3-dihydrobenzofurans with isoxazolines, with good yields and diastereoselectivities.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jie-Hui Zhang, Cheng-Lin Pan, Huan-Huan Zhang, Peng-Fei Xu, Yong-Chun Luo
Summary: A Sc(OTf)3 catalyzed [3 + 2]-annulation reaction has been developed for the conversion of donor-acceptor aziridines and exo-glycals into carbohydrate-spiro-heterocycles, yielding proline analogues and polycyclic compounds. This reaction also revealed the stereochemistry characteristic of the reaction between racemic D-A aziridines and chiral enolethers.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Xuehao Li, Wenwen Cui, Qirong Deng, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: An efficient and environmentally friendly method for synthesizing S-alkyl dithiocarbamates using visible light has been developed. The reaction has a broad substrate scope and good functional group tolerance in water. Importantly, no external photocatalyst is needed, making this method highly promising for applications in pharmaceutical and sulfur chemistry.
Article
Chemistry, Organic
Man Wang, Ming Li, Long Zhang, Ran Song, Daoshan Yang, Jian Lv
Summary: Photoredox catalysis involving Ir-III in combination with DABCO as a dual hydrogen-bonding donor and organic base can enable the direct gamma-C(sp(3))-H activation of saturated alpha-keto esters, leading to the synthesis of various 4-indolyl substituted 2-hydroxy-3-enoic acid esters. This method offers high yields and high enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Wenwen Cui, Yu Li, Xufeng Li, Junxin Li, Xiuyan Song, Jian Lv, Yuan-Ye Jiang, Daoshan Yang
Summary: Transition-metal-catalyzed decarboxylative and C-H functionalization strategies have been extensively studied for the construction of Csp(2)-Csp(2), Csp(2)-Csp(3), and Csp(2)-Csp(3) bonds. However, research on the synthesis of Csp(3)-Csp(3) bonds using this strategy is surprisingly scarce. In this study, an efficient approach for the rapid formation of Csp(3)-Csp(3) bonds through copper-catalyzed decarboxylative Csp(3)-H functionalization is presented. This method offers a promising synthesis method for Csp(3)-Csp(3) bond construction in the field of synthetic and pharmaceutical chemistry.
CHINESE CHEMICAL LETTERS
(2023)
Review
Chemistry, Multidisciplinary
Daoshan Yang, Qiuli Yan, Enjie Zhu, Jian Lv, Wei-Min He
Summary: This review focuses on recent advances in C-S bond formation via visible-light photoredox catalysis, highlighting its potential in pharmaceutical synthesis, synthetic methodology development, and the application of sulfur-containing drugs.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Depeng Duan, Huixin Qiu, Mengdie Tang, Ran Song, Wen Si, Daoshan Yang, Jian Lv
Summary: This study reports a [4+2] cycloaddition catalyzed by Lewis acid HfCl4, leading to high yields of polysubstituted 4H-pyrans. The reaction conditions are mild and exhibit excellent selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Huixin Qiu, Lirong Wen, Jian Lv
Summary: Visible-light-promoted [2+1] and [2+2] cycloaddition reactions of diazocarbonyls with olefins have been developed, and the regioselectivity and reactivity could be controlled by the addition of Rh-2(OAc)(4) in the presence of Ir(ppy)(3) catalyst.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Wenxuan Zhang, Jiaying Sun, Zhendong Lian, Ran Song, Daoshan Yang, Jian Lv
Summary: Here, we report a chiral catalyst-catalyzed asymmetric reaction between 2-alkynyphenols and aromatic ethers. The reaction shows high yield and excellent enantioselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
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, Applied
Ran Song, Caiqi Zhuo, Wen Si, Xiaoying Wu, Tianyi Guan, Daoshan Yang, Jian Lv
Summary: A metal-free method for synthesizing diarylmethylamines was developed using a 1,6-addition reaction of 1-aminobenzotriazole with p-quinone methides catalyzed by triphenylcarbenium tetrafluoroborate. The diarylmethylamines were obtained in moderate to good yields (up to 84%) under mild conditions, and showed unchanged activity after 6 reuses.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Xiaolong Zhu, Xiuyan Song, Xuan Li, Fengxiao Wang, Jian Lv, Min Jiang, Daoshan Yang
Summary: In this manuscript, a radical type ring-opening of sulfonium salts with heteroarenes under visible light conditions is reported. This method does not rely on noble metal photocatalysts or stoichiometric amounts of external oxidants, making it promising for the synthesis of organosulfur compounds and bioactive molecules. The developed photocatalytic system could inspire further applications of sulfonium salts in C(sp(3))-C(sp(2)) bond forming reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Jiaying Sun, Wenxuan Zhang, Ran Song, Daoshan Yang, Jian Lv
Summary: Catalytic direct [4 + 2] cycloaddition reactions and Friedel-Crafts reactions of ortho-alkynylnaphthols with benzofurans have been developed. They afford high yields of functionalized hydrobenzofuro[3,2-b]chromans and hydroarylation products, respectively, with high chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xuan Li, Min Jiang, Junze Zuo, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: This study reports a novel and efficient copper-catalyzed Sonogashira reaction between sulfonium salts and alkynes, promoted by visible light, for the synthesis of internal alkynes. The coexistence of nitrogen and phosphorus ligands in the system is crucial for the success of this reaction.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Ran Song, Zhendong Lian, Wei Feng, Tianyi Guan, Wen Si, Daoshan Yang, Jian Lv
Summary: A novel palladium-catalyzed decarboxylative O-allylation of phenols was developed. A gamma-methylidene-delta-valerolactone (GMDV) was identified as an efficient and selective allylation reagent, leading to the synthesis of allyl phenyl ethers in high yields under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Man Wang, Rui Wang, Long Zhang, Wen Si, Ran Song, Daoshan Yang, Jian Lv
Summary: An efficient solvent-free radical oxyamination reaction has been demonstrated for the modification of carbonyl compounds adjacent to different chalcogens (e.g., S, O, and Se). This method does not require the use of a transition metal catalyst, chemical oxidant, or photocatalyst, and exhibits a wide substrate scope and high functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Qiuli Yan, Wenwen Cui, Junxin Li, Guiyun Xu, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: A highly efficient visible-light promoted benzylation method using riboflavin as a green photocatalyst has been developed for synthesizing C3-benzylated quinoxalin-2(1H)-one derivatives. This method offers a new approach for the synthesis of these derivatives, with potential applications in pharmaceutical and synthetic chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)