Article
Chemistry, Multidisciplinary
Won Jun Jang, Jeongkyu Woo, Jaesook Yun
Summary: The study reported a method to synthesize enantioenriched alkylboron compounds through conjugate addition, which are influenced by two contiguous carbon stereogenic centers, with high yield and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Brigita Mudrakova, Peter Kisszekelyi, Denisa Vargova, Dorota Zakiewicz, Radovan Sebesta
Summary: This paper presents a highly enantio- and diastereoselective tandem transformation method, using Cu-catalyzed conjugate addition of Grignard reagents to heterocyclic Michael acceptors, followed by one-pot trapping of in situ formed enolates with stabilized carbocations or their equivalents. This method allows the installation of structurally attractive substituents on heterocyclic compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Junwen Wang, Jun Li, Yan Wang, Sisi He, Hengzhi You, Fen -Er Chen
Summary: In this study, a polymer-supported chiral heterogeneous copper catalyst was reported, which demonstrated high reactivity and enantioselectivity in asymmetric conjugate addition reactions.
Article
Chemistry, Organic
Ping Zhang, Guo-Li Chai, En-Ze Yao, Li-Xiao Guo, Xue-Yu Liu, Junbiao Chang
Summary: Asymmetric conjugate addition of organic boronic acids to dienones was achieved using chiral catalysts, resulting in high yields of enantiopure bis-adducts with excellent chemoselectivities and enantioselectivities. These catalytic systems demonstrated high efficiency and broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Yu-Chao Wang, Zhao-Xin Xiao, Miao Wang, Shao-Qian Yang, Jin-Biao Liu, Zhi-Tao He
Summary: This study presents modular protocols for 1,5-conjugate addition reactions via palladium hydride catalysis, which has been considered unfeasible. The results show that the 1,5-conjugate addition products can be conveniently transformed into various privileged enantioenriched motifs, indicating the potential applications of this method in synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chihiro Homma, Taichi Kano, Keiji Maruoka
Summary: A bifunctional amino sulfonamide-catalyzed asymmetric conjugate addition of aldehydes to alkenyl alkynyl ketimines has been developed, yielding the desired conjugate adducts with high chemo-, diastereo- and enantioselectivity.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Hu Tian, Hong-Ming Zhang, Liang Yin
Summary: In this article, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and alpha-substituted alpha,beta-unsaturated thioamides is described, which produces a series of chiral selenides with high to excellent enantioselectivity. The reaction shows a broad substrate scope for both selenols and alpha-substituted alpha,beta-unsaturated thioamides. The catalytic system is also successfully used for asymmetric selenation of beta-substituted alpha,beta-unsaturated thioamides. A [Cu-(R,R-P)-TANIAPHOS]-SePh species is identified by Se-77 NMR spectra, with a chemical shift at delta 462 ppm. Furthermore, a {[Cu-(R)-TOL-BINAP]-SePh}(2) species is characterized by X-ray analysis, confirming the formation of Cu-Se bond in the reaction. Finally, the straightforward transformations of the thioamide group to amine and thioester are demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Zhiqian Chang, Huilong Zhu, Changhui Wu, Junhao Xing, Xiaowei Dou
Summary: The enantioselective synthesis of 2-amino-4H-chromenes via cascade rhodium-catalysed conjugate addition/hetero Thorpe-Ziegler reaction achieved moderate to good yields (up to 98%) and high enantioselectivities (up to 92% ee) using a chiral diene-coordinated rhodium complex as the catalyst. This protocol addresses the methodological deficiency in the asymmetric synthesis of 4-aryl 2-amino-4H-chromenes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Applied
Gianluca Casotti, Vincenzo Rositano, Anna Iuliano
Summary: Stabilised arylzinc iodide prepared by direct insertion of zinc into aryl iodides, were successfully applied as nucleophiles in the Hayashi Rh-catalysed enantioselective conjugate addition to enones, with high yields and 99% ee of the addition product. The general applicability of the protocol was confirmed by using different arylzinc iodides and enones, as well as organometallic reagents with both halogen and electrophilic groups.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Changli He, Xiaoxue Tang, Xin He, Yuqiao Zhou, Xiaohua Liu, Xiaoming Feng
Summary: Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles to beta-nitroenones or beta-nitroacrylates was achieved with chiral scandium catalysts. Functionalized 3,3-disubstituted oxindoles, including terminal and internal vinyl groups, were constructed in excellent yields and ee values.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Daniel Rozsar, Alistair J. M. Farley, Iain McLauchlan, Benjamin D. A. Shennan, Ken Yamazaki, Darren J. Dixon
Summary: This article describes the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated alpha,beta-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) superbase. It provides a straightforward approach to the synthesis of pharmaceutically relevant enantioenriched gamma-nitroesters with unprecedented selectivity. The methodology demonstrates broad substrate scope and has been successfully applied on a gram scale with reduced catalyst loading, allowing for catalyst recovery.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jia-Hao Xie, Yi-Ming Hou, Zuolijun Feng, Shu-Li You
Summary: Here, we describe a synthesis method for cyclohexanones with multiple continuous stereocenters by combining copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to cyclic enones with iridium-catalyzed asymmetric allylic substitution reaction. The reaction yields good to excellent results in terms of yield, diastereoselectivity, and enantioselectivity. Unlike previous studies focusing on adjacent stereocenter construction (1,2-position), this reaction achieves stereodivergent construction of nonadjacent stereocenters (1,3-position) by utilizing two chiral catalysts with different enantiomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jin Cui, Raphael Oriez, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: The copper(I)-catalyzed asymmetric vinylogous additions of siloxyfurans to 2-ester-substituted chromones enable concise and enantioselective assembly of chromanone lactones. This method provides a efficient synthesis of chromanone lactones with precise stereochemical control, which can be used for the formal synthesis of secalonic acid A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ming-Hui Xu, Yong-Hai Yuan, Dong-Dong Liang, Xiao-Ming Zhang, Fu-Min Zhang, Yong-Qiang Tu, Ai-Jun Ma, Kun Zhang, Jin-Bao Peng
Summary: A novel spiro-pyrrolidine-derived bifunctional thiourea catalyst has been developed for stereoselective conjugate addition of furfurals to beta,gamma-unsaturated alpha-ketoesters. The rigid spirocyclic framework of the catalyst is essential for highly enantioselective transformation in the asymmetric trienamine catalysis of benzylic C-H functionalization of 5-benzylfurfurals.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Deyuan Meng, Jing He, Woojin Yoon, Hoseop Yun, Jung Tae Han, Jaesook Yun
Summary: In this study, the catalytic 1,6-addition of chiral alkyl copper nucleophiles generated from borylalkenes and a copper-hydride catalyst was successfully conducted under mild conditions. The controlled chemo- and stereoselectivity played a crucial role in the reductive coupling process, resulting in efficient synthesis of asymmetric 1,6-adducts of p-quinone methides through multicomponent and catalytic tandem reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Pei Xu, Yi-Ming Zhu, Xin-Yu Liu, Xiao-Zhou Zhou, Shun-Yi Wang, Shun-Jun Ji
Summary: The study has developed a method for the synthesis of pyrroloisoquinoline derivatives through the formation of two C-C bonds and one C-N bond via radical cascade cyclization in one step.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Jing-Jing Ai, Jian Li, Shun-Jun Ji, Shun-Yi Wang
Summary: This study reports a one-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions to afford selenocarbamates and allyl sulfone compounds. The method has advantages of being environmentally friendly, green, and having high atomic economy.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Xin-Yu Liu, Yan-Wei Zhao, Tian Jiang, Weidong Rao, Shun-Yi Wang
Summary: A new method for the synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF has been developed. This reaction is initiated by the trisulfur radical anion S-3(center dot-), generated in situ from K2(S) in DMF, without the need for transition-metal catalysis or other additives. In addition to forming two C-S bonds, the heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Ying Chen, Fei Wang, Bo-Xi Liu, Wei-Dong Rao, Shun-Yi Wang
Summary: A Ni(ii)-catalyzed reductive cross-coupling reaction has been developed for the synthesis of benzylic sulfides/selenides from oxalates and thiosulfonates/selenosulfonates under mild conditions. The use of oxalates prepared from corresponding alcohols as carbon radical precursors in the reaction provides an easy substrate availability and mild reaction conditions, offering a new method for the preparation of unsymmetrical sulfides/selenides with good functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Multidisciplinary Sciences
Fei Wang, Ying Chen, Weidong Rao, Lutz Ackermann, Shun-Yi Wang
Summary: In this work, the authors present a new method for the synthesis of disulfides through a reductive nickel-catalyzed cross-electrophile coupling of unactivated alkyl bromides with symmetrical tetrasulfides, forming unsymmetrical disulfide intermediates. This approach offers practicality and scalability for disulfide synthesis.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Shi-Yin Tian, Jing-Jing Ai, Jia-Hui Han, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: A photocatalytic synthesis method was developed to simultaneously construct two C-S/Se bonds and one C-C bond without the use of transition metals or other additives, using diphenyl disulfide or diphenyl diselenide as sulfur or selenium sources.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhenguo Zhang, Jun Gu, Yongheng Lv, Liang Ji, Xiaoxiao Liu, Beishen Wu, Fang Liu, Zhenhua Jia, Teck-Peng Loh
Summary: A metal-free synthesis of β-carbolines from tryptamines and aromatic aldehydes is achieved using a triaryl carbenium ion pair as a catalyst. This method exhibits excellent functional group tolerance and is demonstrated with the synthesis of Eudistomin U and fluorescent compounds on a large scale. Mechanistic studies reveal the formation of a trityl radical through a single-electron transfer process and its trapping by an oxygen molecule. In addition, an in-situ-generated reactive oxygen-centered radical is found to be essential for the efficient dehydroaromatization process.
CELL REPORTS PHYSICAL SCIENCE
(2023)
Article
Chemistry, Organic
Ying Chen, Fei Wang, Weidong Rao, Shusu Shen, Daopeng Sheng, Shun-Yi Wang
Summary: An efficient method for the copper-catalyzed ring-opening hydrolysis of silacyclobutanes to silanols was developed in this study. This strategy offers the advantages of friendly reaction conditions, simple operation, and good functional group compatibility. It also allows for the introduction of S-S bonds into organosilanol compounds in a single step. The successful gram scale synthesis demonstrates the potential of this protocol for practical industrial applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Letter
Chemistry, Organic
Yi-Fan Jiang, Wei-Chen Zhu, Xin-Yu Liu, Shi-Yin Tian, Jia-Hui Han, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: Here, a new method is provided to synthesize 1,3-dibenzenesulfonylpolysulfane (DBSPS), which reacts with boronic acids to produce thiosulfonates. Commercially available boron compounds significantly expand the range of thiosulfonates. Experimental and theoretical investigations reveal that DBSPS can generate both thiosulfone and dithiosulfone fragments, with the latter being unstable and decomposing into thiosulfonates.
Article
Chemistry, Organic
Wang Chen, Xin-yu Liu, Daopeng Sheng, Yi-Fan Jiang, Weidong Rao, Shu-Su Shen, Zhao-Ying Yang, Shun-Yi Wang
Summary: A nickel-catalyzed C-SS reductive cross-coupling reaction for producing unsymmetric disulfides has been developed. This approach exhibits a broad substrate scope, excellent functional group tolerance, and can be conducted under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Jia-Hui Han, Shi-Yin Tian, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: In this study, a visible-light-mediated selenylation/cyclization reaction using selenium radicals generated from diselenides as radical sources with acrylimide derivatives is described. This method provides a mild and effective approach for the synthesis of symmetrical selenosubstituted pyrrolidine-2,5-diones. The described catalytic strategy offers advantages such as mild reaction conditions, metal-free conditions, no additives required, easy operation, and a wide substrate range.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fei Wang, Ying Chen, Weidong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A Cu-catalyzed cascade reaction has been developed for the construction of S (Se)-containing organosilicon compounds using four-membered silacyclobutanes (SCBs) and thiosulfonates. The protocol exhibits a wide substrate scope, high functional group compatibility, and mild reaction conditions, enabling the formation of new C-S (Se) and Si-O bonds in a single step.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ying Chen, Daopeng Sheng, Fei Wang, Weidong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A Ni(II)/TPMPP-catalyzed reductive cross-coupling reaction has been reported for the synthesis of unsymmetric disulfides from benzyl oxalates and tetrasulfides. This method offers mild reaction conditions, wide substrate range, and easy operation, and has successfully achieved gram-scale synthesis of disulfides.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fei Wang, Ying Chen, Lutz Ackermann, Shun-Yi Wang
Summary: In this study, a selective cross-coupling reaction between unactivated alkyl bromides and diaryl tellurides was achieved using reductive nickel catalysis, leading to the synthesis of unsymmetrical alkyl-aryl tellurides with mild reaction conditions, high yields, easily accessible substrates, and a broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Bo-Xi Liu, Fei Wang, Ying Chen, Wei-Dong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A visible-light-promoted regioselective denitrogenative cross-coupling between benzotriazinones and selenosulfonates has been developed for the synthesis of ortho-selenylated benzamides. The reaction provides good yields and demonstrates a general substrate scope. Furthermore, this protocol has been successfully employed for the one-pot two-step synthesis of a series of ebselen and its analogs.
ORGANIC CHEMISTRY FRONTIERS
(2022)
