Article
Chemistry, Organic
Jun-Li Li, Hao-Yuan Li, Shan-Shan Zhang, Shigang Shen, Xiu-Long Yang, Xiaoying Niu
Summary: An efficient oxidant-free, photoredox-mediated cascade cyclization strategy has been developed for the synthesis of 1,3,4-oxadiazoles. This transformation can be achieved by using an organo acridinium photocatalyst and a cobaloxime catalyst, resulting in high yields of the desired products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Huan Zhang, Enhui Wang, Shasha Geng, Zhengli Liu, Yun He, Qian Peng, Zhang Feng
Summary: The iron-catalyzed defluorosilylation reaction is an efficient, highly functional-group compatible, and stereo- and regioselective reaction that can be used for late-stage silylation of biologically relevant compounds, offering opportunities for applications in medicinal chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Jie Shi, Li-Yun Guo, Qu-Ping Hu, Yu-Tao Liu, Qing Li, Fei Pan
Summary: A photoredox-catalyzed radical cascade reaction has been developed for the synthesis of lactam-substituted gem-difluoroalkenes, providing a simple method with good functional group tolerance and high yields.
Article
Chemistry, Organic
Jibin Li, Zheng Liang, Yuzhi Ren, Jian Gao, Ding Du
Summary: A new class of functionalized gem-difluorocyclopropanes bearing acyl groups was synthesized via the N-heterocyclic carbene catalyzed difluorocyclopropanation of alkenes with aldehydes and CF2Br2. This reaction involves a cascade three-component radical relay/intramolecular cyclization process. The protocol features metal- and photocatalyst-free reaction conditions, readily accessible starting materials, good functional group tolerance, and easy scalability. Moreover, this strategy is appealing to pharmaceutical chemistry because it is potentially useful in constructing and modifying bioactive molecules via late-stage functionalization.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yuyang Bai, Liping Cao, Siyuan Li, Guang'an Zhang, Yingguo Liu, Fengqian Zhao, Junliang Wu
Summary: A photoredox/Lewis acid cooperative catalytic system has been developed for the construction of C-vinyl-C-Rf bonds through the dehydrative difluoroalkylation of benzyl alcohols. Various allylic gem-difluorides were obtained with moderate yields and good to excellent E/Z selectivity. Control experiments were conducted and a possible mechanism for this process was proposed.
Article
Chemistry, Organic
Yanhui Wang, Gavin Chit Tsui
Summary: A highly diastereoselective Pd(0)-catalyzed Mizoroki-Heck reaction of gem-difluoroalkenes is reported. This reaction allows for cross-coupling of a C-F and C-H bond by reacting two different alkenes through a distinct pathway. Mono-fluorinated 1,3-diene products can be synthesized with control over each alkene's geometry and good functional group tolerance.
Article
Chemistry, Organic
Xue Zhang, Zhen Luo, Tang-Lin Liu, Qing-Hua Li
Summary: The functional group migration strategy enables the construction of complex structures from simple starting materials. While 1,3-hydride migration in intramolecular reactions is well-established, 1,3-carbon migration in allylic alcohols is less reported. In this study, a Ru-catalyzed 1,3-indolyl migration protocol under mild conditions is developed, which allows for the synthesis of β-indolyl ketones with a broad substrate scope and reasonable yields through selective C(sp(3))-C(sp(2)) bond cleavage and reconstruction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Shu-Hui Lei, Ya Zhong, Xian-Peng Cai, Qing Huang, Jian-Ping Qu, Yan-Biao Kang
Summary: A simple and practical method for the preparation of beta-O substituted aldehydes directly from linear allylic esters has been developed. By using a specific catalyst and oxidant, the reaction proceeds smoothly to give the desired products, showing broad substrate scope and excellent regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Pan Xie, Cheng Xue, Junfei Luo, Sanshan Shi, Dongdong Du
Summary: The study presents a green and sustainable strategy for the selective cleavage of C = C double bonds in aryl olefins using solar energy, air as the oxidant, and water as the solvent. Various aryl olefins showed good tolerance in this method and yielded the desired carbonyl products in satisfactory yields. The homogeneous catalytic system used in the reaction could also be reused and retained good activity even after repeating three times, with involvement of O-2(-) and O-1(2) in the reaction and proposed mechanisms involving electron transfer and energy transfer pathways based on mechanism investigations.
Article
Chemistry, Organic
Songlin Yan, Weijie Yu, Jianye Zhang, Hongmei Fan, Zhifeng Lu, Zhenming Zhang, Tao Wang
Summary: An organic photoredox-catalyzed gem-difluoroallylation of alpha-trifluoromethyl alkenes with alkyl iodides via C-F bond cleavage for the synthesis of gem-difluoroalkene derivatives is reported. The transition-metal-free transformation utilized a readily available organic dye as the sole photocatalyst and provided good to high yields with a variety of iodides, including primary, secondary, and tertiary alkyl iodides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yong Wang, Yuxuan Li, Lei Wang, Shengtao Ding, Lijuan Song, Xinhao Zhang, Yun-Dong Wu, Jianwei Sun
Summary: In this study, a new method for efficient construction of gem-diboryl compounds with hetero-substituted carbon centers was developed. This method involves the alpha-dihydroboration of heteroalkynes and is a practical and atom-economic alternative to the conventional multistep synthetic strategy.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Dong Yi, Linying He, Zhongyu Qi, Zhijie Zhang, Mengshun Li, Ji Lu, Jun Wei, Xi Du, Qiang Fu, Siping Wei
Summary: Alkoxy radical-mediated carbon-carbon bond cleavage is an effective synthetic strategy that allows for selective cleavage of carbon-carbon bonds, providing a convenient route for the synthesis of valuable compounds and enabling the construction of complex molecular architectures.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Zachary P. Sercel, Alexander W. Sun, Brian M. Stoltz
Summary: Enantioenriched gem-disubstituted 4-imidazolidinones were prepared in high yield and high enantioselectivity through Pd-catalyzed decarboxylative asymmetric allylic alkylation. A rapid synthetic route starting from 2-thiohydantoin was developed, and the orthogonality of the protecting groups used for nitrogen-rich products was demonstrated, indicating potential applications in drug design.
Article
Chemistry, Multidisciplinary
Jianxiao Li, Chenjing Hong, Yanan Niu, Bowen Wang, Wenfang Xiong, Huanfeng Jiang
Summary: A novel and reliable palladium-catalyzed oxylallylation reaction was developed for the synthesis of gem-difluorinated isoxazole derivatives. This strategy enables the direct combination of isoxazole motifs and gem-difluoroalkene units, which is challenging to achieve through conventional synthetic methods. The reaction proceeded with high atom- and step-economy and excellent functional group compatibility, providing structurally diverse products in moderate to good yields.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Lin Zhu, Jie Huang, Fanling Meng, Ziyun Tan, Xiao Meng, Yang Xiao, Lanlan Zhang, Wenyi Li, Chao Wang
Summary: A NiH-catalyzed migratory and non-migratory gem-difluoroallylation reaction of alkenyl amines with trifluoromethyl alkenes has been developed. This reaction offers high selectivity and diversity for the synthesis of fluoro-containing amines, which is beneficial for drug discovery.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Xing-Xing Zhu, Huai-Qin Wang, Chen-Guang Li, Xiao-Lan Xu, Jun Xu, Jian-Jun Dai, Hua-Jian Xu
Summary: The study presents a novel electrochemical trifluoromethylation method for thiophenols without the use of metal catalysts and oxidants. The reaction conditions are mild, substrates are readily available, and moderate to good yields can be achieved. Furthermore, this protocol can be easily scaled up with moderate efficiency.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jian-Jun Dai, Xin-Xin Teng, Wen Fang, Jun Xu, Hua-Jian Xu
Summary: An electrochemically promoted decarboxylative borylation reaction is reported, which can proceed under mild conditions without the use of transition metal- or photo-catalysts. The key feature of this reaction is the compatibility of diboron reagents with the electrochemical conditions. It exhibits broad substrate scope, good functional group tolerability, and easy scalability.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Jun Xu, Chao Peng, Bolin Yao, Hua-Jian Xu, Qiang Xie
Summary: This report describes a method for the deoxyfluorination of alcohols using KF as the fluorine source via in situ generation of highly active CF3SO2F. Diverse functionalities, including halogen, nitro, ketone, ester, alkene, and alkyne, are well tolerated. The mild conditions, short reaction time, and wide substrate scope make this method an excellent choice for constructing C-F bonds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Lei Xu, Zheng Dong, Qi Zhang, Ning Deng, Shi-Yu Li, Hua-Jian Xu
Summary: This article introduces new methods for Miyaura borylation and protoboration of alkynes catalyzed by low loadings of palladium, which have a broad substrate scope, good functional-group compatibility, and gram-scale synthetic ability.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Fei Tang, Yi-Si Feng, Zhi-Fei Cheng, Qi Zhang, Hua-Jian Xu
Summary: We report a copper metallaphotocatalytic 1,2-difunctionalization of terminal alkynes with N-hydroxyphthalimide (NHP) esters and readily available silyl reagents (TMSCN and TMSNCS) to access stereodefined trisubstituted alkenes, including (E)-alkenyl nitriles and thiocyanates. The reaction proceeds with excellent anti-stereoselectivity and demonstrates broad compatibility with a wide range of terminal alkynes and NHP esters as alkyl radical precursors. Experimental and computational studies have been performed to gain insight into the reaction mechanism.
Article
Multidisciplinary Sciences
Jian-Jun Dai, Xianglin Yin, Lei Li, Mario E. Rivera, Ye-Cheng Wang, Mingji Dai
Summary: This study presents a modular and practical diamination of allenes, allowing for efficient syntheses of beta,gamma-diamino carboxylates and sulfones. The reaction exhibits broad substrate scope, excellent functional group tolerability, and scalability.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Jun Xu, Jia-Wei Liu, Rui Wang, Jian Yang, Kui-Kui Zhao, Hua-Jian Xu
Summary: The conversion of easily available trifluoromethylarenes through C-F bond activation provides a rapid pathway for accessing difluorobenzylic substructures, which is important in the production of pharmaceuticals and agrochemicals. However, the current advances in this field have been limited to the construction of C-C-(H) bonds, thus restricting the diversity of accessible motifs. The selective formation of a carbon-heteroatom bond via C-F bond functionalization remains a challenging synthetic task, but it enables the direct synthesis of medicinally interesting aryldifluoromethyl ether [ArCF2X- (X= S, O, or Se)] scaffolds.
Article
Chemistry, Organic
Jiwei Wu, Yuting Zhang, Jingyi Yang, Lingxiang Yu, Shaoqing Zhang, Jie Zhou, Zirong Li, Xiaolan Xu, Huajian Xu
Summary: A novel method for the synthesis of formamides through the decarboxylative N-formylation of amines with glyoxylic acid has been developed. This method provides an efficient protocol for the synthesis of various formamides with moderate to excellent yields, and it can accommodate a wide range of functional groups under metal free and base free conditions. Moreover, the large-scale experiments and high chemoselectivity have shown great potential application of this strategy.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wei Zhou, Zhi-Wen Luo, Hua Xiao, Jun Yi, Jian-Jun Dai
Summary: In this study, a photo-induced radical reaction was developed to convert vinylboronic esters into alkylboronic esters using CuCl2 as a catalyst. The method features mild reaction conditions, easily accessible reagents, and scalability for gram-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Le Zhang, Ye Liu, Chao-Xu Li, Lei Zhu, Guo-Yin Xiong, Shi-Lu Fan, Jian-Jun Dai, Hua Xiao
Summary: A phosphine-promoted tandem Diels-Alder reaction using pentadienyl 4-nitrobenzoate as a diene precursor with 3-olefinic oxindoles or CF3-activated ketones as dienophiles has been developed. This method provides a metal-free and step-efficient approach for synthesizing exomethylene-bearing spirooxindoles and dihydropyrans, which are privileged structures found in natural products.
Article
Chemistry, Multidisciplinary
Wen Fang, Huai-Qin Wang, Wei Zhou, Zhi-Wen Luo, Jian-Jun Dai
Summary: In this study, a photoinduced, CuCl2 mediated C(sp(3))-H borylation of unactivated alkanes is reported. This method offers mild reaction conditions, readily available reagents, and gram-scale scalability.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Zheng Dong, Ren-Jie Tong, Lei Xu, Hua-Jian Xu, Jun Xu
Summary: The synthesis of (deuterated) 1,1-disubstituted alkenes via Pd-catalyzed decarboxylative hydroarylation of alkynyl carboxylic acids with arylboronic acids has been developed. The reaction features excellent regioselectivity, a broad substrate scope and gram-scale synthetic ability and offers a general synthetic method to synthesize 1,1-dideuterio olefins. Preliminary mechanism investigations indicate that 1,1-disubstituted alkenes are formed by hydroarylation of terminal alkynes generated by in situ decarboxylation of alkynyl carboxylic acids.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jun Xu, Li Liu, Zhao-Cheng Yan, Yang Liu, Long Qin, Ning Deng, Hua-Jian Xu
Summary: In this research, a photoredox-catalyzed hydroxyalkylation method was developed for azole derivatives with aldehydes in the aqueous phase under an air atmosphere. Additionally, the catalytic system was also suitable for the alkylation of azole derivatives with alkanes. This methodology is environmentally friendly, requires no external additive, and exhibits good functional group compatibility.
Article
Chemistry, Multidisciplinary
Wei Liu, Le Zhang, Ye Liu, Shi-Lu Fan, Jian-Jun Dai, Wei Tao, Hui-Xia Zhu, Hua Xiao
Summary: In this study, a consecutive S(N)2'/S(N)2'' addition of phenol to gamma-vinyl MBH carbonate was performed, leading to the formation of functionalized exocyclohexenes with excellent chemoselectivity. Additionally, using o-hydroxychalcones as pronucleophiles, a series of pharmaceutically intriguing tricyclic chromane derivatives were selectively synthesized through an S(N)2'/S(N)2''/intramolecular Diels-Alder reaction sequence with good diastereoselectivity.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Cheng Wu, Xiao Shen, Jianjun Dai, Jun Xu, Huajian Xu
Summary: By utilizing a direct nucleophilic substitution reaction under transition metal free conditions, easily available aryl and alkyl thiocyanates were converted into the desired products, enabling the synthesis of (benzenesulfonyl)difluoromethyl thioethers.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
