Article
Chemistry, Multidisciplinary
Cui-Tian Wang, Peng-Yu Liang, Ming Li, Bin Wang, Yu-Zhao Wang, Xue-Song Li, Wan-Xu Wei, Xue-Ya Gou, Ya-Nan Ding, Zhe Zhang, Yu-Ke Li, Xue-Yuan Liu, Yong-Min Liang
Summary: The aryl-to-vinyl nickel 1,4-migration (1,4-Ni migration) reaction has been reported for the first time. It involves a tandem reaction that delivers trisubstituted olefins by reductive coupling of alkenyl Ni species with unactivated brominated alkanes. This reaction exhibits mild conditions, high selectivity, and the intermediates do not isomerize.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Youxiang Jin, Hao Wen, Feiyan Yang, Decai Ding, Chuan Wang
Summary: In this study, a cross-electrophile strategy was successfully applied to synthesize multisubstituted allenes. Nickel-catalyzed reductive cross-coupling between propargyl carbonates and organoiodides provided a method to prepare tri- or tetrasubstituted allenes without the need for pregenerated organometallics. Furthermore, propargyl carbonates were found to be suitable allenylating agents in nickel-catalyzed asymmetric reductive aryl-allenylation, leading to the formation of chiral benzene-fused cyclic compounds with a quaternary allenyl-substituted stereogenic center in a highly enantioselective manner.
Article
Chemistry, Organic
Sudip Shit, Bipin Kumar Behera, Subhamoy Biswas, Anil K. K. Saikia
Summary: A metal-free Lewis acid-initiated protocol has been developed for the synthesis of highly substituted 3-(dihydrofuran-3(2H)-ylidene)isobenzofuran-1(3H)-imines. The reaction involves the formation of dihydrofuranylidene carbocation followed by intramolecular cyclization, leading to the desired products in moderate to good yields. The methodology can also be extended to the synthesis of 3-(dihydro-2H-pyran-3(4H)-ylidene)-isobenzofuran-1(3H)-imines, and furanylidene isobenzofuranones can be obtained in excellent yields through post synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Gyumin Kang, Sunkyu Han
Summary: In this study, we successfully synthesized dimeric high-oxidation-state securinega alkaloid Flueggeacosine B via two synthetic routes. The second-generation synthesis was more streamlined and a new reaction was developed to provide a direct pathway for the synthesis of compounds with a conjugated dicarbonyl moiety.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Weitao Hu, Zhiyang Lin, Chuan Wang
Summary: Here, we describe a nickel-catalyzed cross-electrophile ring-opening reaction of vinyl epoxides, where aryl iodides, alkyl iodides, and benzyl chlorides can all be used as electrophilic coupling partners, providing a new approach to preparing multisubstituted allylic alcohols. This method exhibits broad substrate scope, good step-economy, high selectivity, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Yan-Long Zheng, Di-Yu Liang, Hong-Bin Ma, Fan-Cheng Meng, Tie Wang
Summary: A NiH-catalyzed polarity-reversed hydroamination of unsaturated alkenes with electrophilic anthranils was developed, providing a regio- and chemoselective synthesis of γ,δ and C-arylamines with carbonyl or alcohol functionality, achieving 100% atom efficiency.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Sushree Ranjan Sahoo, Biswajit Das, Debayan Sarkar, Hans Reuter
Summary: A temperature-controlled synthesis of multi-substituted 4-alkynyl/trans 4-alkenyl coumarins was achieved using a metal salt cascade approach. Water served as both a nucleophile and a hydrogen source, while the presence of a metal salt facilitated the reduction of alkyne. This method overcomes the structural shortcomings of existing Sonogashira and Heck coupling reactions. Furthermore, the obtained 2,3-disubstituted coumarins can be easily converted into 2,3-disubstituted dihydrocoumarins, which are important building blocks in organic transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jin Zhang, Pei Zhang, Yangmin Ma, Michal Szostak
Summary: This study reports a novel solvent-free method for synthesizing ketones with high selectivity from acyl chlorides and boronic acids. The reaction takes place in the solid state, without the use of solvents, and has a short reaction time, demonstrating excellent selectivity for C(acyl)-Cl bond cleavage.
Article
Chemistry, Organic
Xingwang Deng, Guan Zhou, Xiao Han, Khadim Ullah, Rajavel Srinivasan
Summary: Potassium acyltrifluoroborates (KATs) are opening up new avenues in chemical biology, materials science, and synthetic organic chemistry due to their intriguing reactivities. The chemoselective Pd-catalyzed approaches developed for the late-stage diversification of arenes bearing prefunctionalized KATs feature chemoselective cross-coupling, rapid diversification, functional group tolerance, mild reaction conditions, simple operation, and high yields.
Article
Chemistry, Organic
Jianwen Jin, Andres Felipe Leon Rojas, Yichao Zhao, Sara Helen Kyne, Bo Xia, Bingwei Zhong, Philip Wai Hong Chan
Summary: This study presents a synthetic method for efficiently preparing (E)-3-arylazoindoles, which does not require the exclusion of air or moisture and can be conducted under mild reaction conditions. The suggested mechanistic pathway of the azo coupling reaction reveals the unique electrophilic behavior of α-diazocarbonyl compounds. Experimental studies provide insights into the preferential generation of a (1H-indol-3-yl)gold species and its impact on the regio- and chemoselectivity of the products. The utility of this synthetic method has been demonstrated in the synthesis of specific molecules, molecular switch assembly, and late-stage functionalization of biologically relevant molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Chao Wang, Yu-Chao Liu, Meng-Yu Xu, Bin Xiao
Summary: An unprecedented cross-coupling reaction of alkyl carbagermatranes with bromofluoroolefins was achieved to deliver dialkyl-substituted monofluoroalkenes, providing an opportunity for challenging molecules with excellent functional group tolerance. The utility of this strategy was demonstrated through the preparation of bioactive agent analogues, including antitubercular agent mimics and COX-2 inhibitor analogues, as well as late-stage fluoroalkenylation of drug-molecule derivatives.
Article
Chemistry, Multidisciplinary
Baichuan Mo, Chunxia Chen, Jinsong Peng
Summary: Various multi-substituted pyrido[1,2-a]pyrimidin-4-ones were synthesized through a one-pot tandem CuI-catalyzed C-N bond formation/intramolecular amidation reaction at 130 °C in DMF. This protocol allows for practical and modular synthesis of pyrido[1,2-a]pyrimidin-4-ones from readily available 2-halopyridine and (Z)-3-amino-3-arylacrylate ester in good to excellent yields, with simple operation, broad substrate scope, good functional group tolerance, and gram scale preparation.
Article
Chemistry, Organic
Kirsten A. Hewitt, Claire A. Herbert, Elizabeth R. Jarvo
Summary: A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been developed for the synthesis of 3,5-vicinal carbocyclic rings found in various biologically active compounds and natural products. Mechanistic experiments suggest that the reaction proceeds through alkyl iodides formed in situ, initiates at the secondary electrophilic center, and proceeds via radical intermediates.
Article
Chemistry, Organic
Tingting Yan, Kaki Raveendra Babu, Yong Wu, Yang Li, Yuhai Tang, Silong Xu
Summary: A phosphine-catalyzed olefinic cross-coupling reaction between benzyl halides and fumarates has been described, providing trisubstituted alkenes with good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.
Article
Chemistry, Physical
Zi-Chao Wang, Xiaohua Luo, Jia-Wen Zhang, Chen-Fei Liu, Ming Joo Koh, Shi-Liang Shi
Summary: Metal-catalysed cross-coupling reactions play a central role in modern chemical synthesis. In this study, a highly enantio- and regioselective three-component cross-coupling of unactivated alkenes with aryl or alkenyl triflates and organometallics was achieved by using nickel catalysts bearing bulky C2-symmetric chiral N-heterocyclic carbene ligands. This strategy provides a general and modular platform for upgrading feedstock alkenes to value-added molecules.
Review
Chemistry, Multidisciplinary
Tao Yu, Zhengwei Ding, Wenzheng Nie, Jiao Jiao, Hailong Zhang, Qian Zhang, Chao Xue, Xinhua Duan, Yoichi M. A. Yamada, Pengfei Li
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Editorial Material
Chemistry, Multidisciplinary
Miao Zhan, Peidong Song, Jiao Jiao, Pengfei Li
CHINESE JOURNAL OF CHEMISTRY
(2020)
Review
Chemistry, Multidisciplinary
Tao Yu, Jiao Jiao, Peidong Song, Wenzheng Nie, Chunhai Yi, Qian Zhang, Pengfei Li
Article
Biochemistry & Molecular Biology
Takumi Ishida, Yuta Sawanaka, Ryota Toyama, Zhenfei Ji, Hiroki Mori, Yasushi Nishihara
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2020)
Article
Chemistry, Organic
Xiu Wang, Zhenhua Wang, Takumi Ishida, Yasushi Nishihara
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Liyan Fu, Qiang Chen, Yasushi Nishihara
Review
Chemistry, Multidisciplinary
Jiao Jiao, Wenzheng Nie, Tao Yu, Fan Yang, Qian Zhang, Feierdaiweisi Aihemaiti, Tingjun Yang, Xuanyu Liu, Jiachen Wang, Pengfei Li
Summary: Continuous-flow multi-step synthesis utilizes microchannel flow chemistry to transform traditional organic synthesis, requiring innovative methods to address challenges. Recent years have seen significant progress with green reactions, telescoped design, and novel separation techniques, leading to successful preparation of complex APIs.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Linghua Wang, Saima Perveen, Yizhao Ouyang, Shuai Zhang, Jiao Jiao, Gang He, Yong Nie, Pengfei Li
Summary: A novel nickel(II)-carborane complex catalyst has been reported in this study, allowing for selective carbene transfer reactions under low catalyst loading and mild conditions, effective for various types of reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Peidong Song, Linlin Hu, Tao Yu, Jiao Jiao, Yangqing He, Liang Xu, Pengfei Li
Summary: This study introduces a new tunable chiral pyridine framework, which is successfully applied in a highly selective iridium-catalyzed reaction with high yields. Experimental and theoretical investigations demonstrate the excellent performance of this framework, which can be used in the synthesis of chiral protonated compounds.
Article
Chemistry, Organic
Dongqiu Li, Fang Cheng, Yuhai Tang, Jing Li, Yang Li, Jiao Jiao, Silong Xu
Summary: The method described involves a phosphine-catalyzed internal redox [4 + 2] annulation of 1,4-enynoates with electron-deficient alkenes, resulting in the efficient synthesis of highly functionalized cyclohexenes with exclusive regioselectivity and high diastereoselectivity under mild conditions.
Article
Chemistry, Organic
Qin Wang, Yan Shi, Xiaoli Huang, Yongzhuang Wang, Jiao Jiao, Yuhai Tang, Jing Li, Silong Xu, Yang Li
Summary: A highly efficient Ru(II)-catalyzed regio- and stereospecific hydro-oxycarbonylation reaction has been developed for unsymmetrical internal alkynes bearing a difunctional 2-pyridyloxy directing group with carboxylic acids. This reaction provides allylic (Z)-enol esters in good to excellent yields with a broad substrate scope under mild conditions. The difunctional directing group can be diversely derivatized, particularly allowing for allylic substitution with various nucleophiles to afford beta-functionalized (Z)-enol esters without directing groups.
Article
Chemistry, Organic
Yang Li, Yongzhuang Wang, Xiaoli Huang, Yan Shi, Yuhai Tang, Jiao Jiao, Jing Li, Silong Xu
Summary: This highly efficient cascade cyclization reaction features a Ru(II)-catalyzed C-H activation initiated indole formation/Diels-Alder reaction/iminium ion cyclization sequence, providing hexacyclic indolines as single diastereomer in good to excellent yields with a broad substrate scope under mild conditions. The reaction allows for the simultaneous generation of five new chemical bonds and four new rings in one pot, offering a rapid and concise approach toward synthesizing polycyclic indoline alkaloids and their analogues.
Article
Chemistry, Organic
Xiaoli Huang, Yan Shi, Yongzhuang Wang, Jiao Jiao, Yuhai Tang, Jing Li, Silong Xu, Yang Li
Summary: A rhodium-catalyzed diastereoselective formal [5 + 2] annulation of indoles with cyclohexadienone-containing 1,6-enynes has been successfully established via indole 2,3-difunctionalization. This method allows for rapid construction of indole-fused oxepines with a broad substrate scope and simultaneous formation of cis-hydrobenzo[b] oxepine scaffolds, which are core units found in natural products with important biological activities.
Article
Chemistry, Organic
Dongqiu Li, Fang Cheng, Yuhai Tang, Jing Li, Yang Li, Jiao Jiao, Silong Xu
Summary: In this study, we describe a DABCO-catalyzed [4 + 2] annulation reaction between 5-methylenehex-2-ynedioates and electron-deficient olefins, which leads to the formation of functionalized cyclohexadienes in good yields under mild reaction conditions. The incorporation of the beta- and epsilon-carbons of the substrates for C-C bond formation represents a novel reactivity different from previous reports. It is believed that the annulation proceeds through a domino cyclization initiated by a cross Rauhut-Currier reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jiao Jiao, Wenzheng Nie, Peidong Song, Pengfei Li
Summary: A new air-stable Si,S-chelating ligand has been developed and successfully utilized in iridium-catalyzed ortho C-H borylation reaction with a broad substrate scope, providing a rapid, efficient, and economic method for the preparation of organoboron compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
