Article
Chemistry, Organic
Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li
Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Kokila Sakthivel, R. J. Gana, Toshitaka Shoji, Naoko Takenaga, Toshifumi Dohi, Fateh V. Singh
Summary: This study demonstrates the effectiveness of metal catalysts in multicomponent reactions and provides an overview for their safe application in MCRs.
FRONTIERS IN CHEMISTRY
(2023)
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, Organic
Jiaying Lv, Huixin Liu, Le Lu, Ruimao Hua
Summary: In this study, benzo[b]fluorenes were synthesized via cascade reactions, involving the formation of the benzoenyne-allene intermediate and its subsequent cyclization. Density functional theory calculation was used to determine the energy difference for the formation of the final products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shigeru Arai, Saki Inagaki, Masaya Nakajima, Atsushi Nishida
Summary: Vinylallenes have been recognized as versatile C2 and C4 components for nickel-catalyzed intramolecular [4+2] and [2+2] cycloadditions, with up to 90% yield for the former and up to 88% yield for the latter. DFT studies revealed a concerted mechanism involving the activation of different C-C multiple bonds in the substrates for both reaction pathways.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Dhananjay Chaudhary, Suman Yadav, Naveen Kumar Maurya, Dharmendra Kumar, Km Ishu, Malleswara Rao Kuram
Summary: This article describes a mild reaction method for the synthesis of regiodivergent Indole and Indoline derivatives, controlled by the N-protecting group, with a broad substrate scope and a functionalizable olefinic moiety.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Raffaella Mancuso, Melania Lettieri, Ida Ziccarelli, Patrizio Russo, Antonio Palumbo Piccionello, Bartolo Gabriele
Summary: A catalytic carbonylative approach is presented for the multicomponent synthesis of benzothiophene derivatives, based on an S-cyclization-demethylation-alkoxycarbonylation-reduction sequence promoted by the PdI2/KI catalytic system under relatively mild conditions. Benzothiophene-2-acetic esters are obtained in moderate to good yields starting from variously substituted substrates in combination with different alcohols as external nucleophiles.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Run-Duo Gao, Scott A. Shuler, Donald A. Watson
Summary: The study presents a novel palladium-catalyzed tandem reaction for the synthesis of complex, stereogenic secondary lactams from O-phenyl hydroxamic ethers. The reactions exhibit outstanding functional group tolerance and high diastereoselectivity.
Article
Chemistry, Organic
Nuan Chen, Ting Zhou, Hong Zhang, Yuqi Zhu, Ming Lang, Jian Wang, Shiyong Peng
Summary: An unprecedented copper-catalyzed tandem reaction of 1,6-enynes with diazo compounds via a cross-coupling/[2 + 2] cycloaddition sequence was reported, leading to the synthesis of a library of methylenecyclobutane-fused ring systems with high proximal-regioselectivity and diastereoselectivity. Moreover, the key intermediate of 1,6-allenene proceeds via a thermally promoted [2 + 2] cycloaddition in the absence of copper catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qing Yang, Xiao-Tong Yan, Cheng-Tao Feng, De-Xiang Chen, Zhong-Zhong Yan, Kun Xu
Summary: This multicomponent reaction successfully achieved the single-step construction of cyano-functionalized imidazo[1,5-a]pyridines with molecular diversity, with the use of NH4SCN as a safer alternative cyanating agent. The protocol shows great potential for future applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Man Li, Ying Wang, Yunhe Xu
Summary: The palladium-catalyzed intramolecular Heck tandem cyclization reactions efficiently convert 3-substituted indoleamide derivatives to bridged N-heterocyclic products in good yields under simple reaction conditions. The tandem reactions are characterized by the effective construction of fused ring compounds in one pot and good functional group compatibility.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Caijin Zeng, Shaoting Su, Songjia Fang, Huangfeng Jiang, Shaorong Yang, Wanqing Wu
Summary: A novel palladium-catalyzed three-component carbonylation reaction has been developed for the efficient assembly of 1,3-substituted maleimides from haloalkynes and simple anilines. The reaction exhibits high chemo- and regioselectivities, and operates under mild conditions.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Physical
Reshma Babu, Subarna S. Padhy, Ganesan Sivakumar, Ekambaram Balaraman
Summary: Sustainable chemical production requires new catalysts and technologies, and the development of robust catalytic systems based on plentiful transition metals is crucial.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Organic
Qi Li, Zi-Lu Wang, Huan-Xuan Lu, Yun-He Xu
Summary: A copper-catalyzed 1,4-protosilylation of alpha-alkynyl-enones has been developed to prepare functionalized chiral homoallenylsilanes with a contiguous stereogenic center and axis, showing good yields and excellent enantioselectivities and diastereoselectivities.
Article
Chemistry, Physical
Jiangjie Zhang, Jun Ying, Xiao-Feng Wu
Summary: A novel palladium-catalyzed tandem cyclization and carbonylation reaction was developed for the synthesis of indeno[1,2-b]indol-10(5H)-one derivatives. The reaction proceeded smoothly with high yields using formic acid as the CO source. This method can also be applied for the modification of various bioactive molecules.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Sifan Li, Wei Shu
Summary: Fluorine-containing molecules have wide applications in pharmaceutical and agrochemical industries due to the ability to tune the biological activities. Recent research focuses on selectively cleaving C-sp(3)-F bonds in multifluorinated compounds for synthesis, with radical reactions offering the potential for selective functionalizations.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Ming-Shang Liu, Hai-Wu Du, Wei Shu
Summary: A transition-metal-free protocol for selective allylic C-H nitrogenation, oxygenation, and carbonation of alkenes has been developed, providing multialkyl substituted allylic amines, ammonium salts, sulfonyl amides, esters, and ethers in good yields. The reaction shows excellent functional group tolerance and can be applied to the late-stage allylation of natural products, drug molecules, and peptides with high chemoselectivity.
Article
Chemistry, Multidisciplinary
Bi-Hong Chen, Yi-Dan Du, Wei Shu
Summary: Herein, a metal-free photocatalytic regioselective C-H alkylation method for electron-rich arenes with both activated and unactivated alkenes was developed, providing a general and straightforward metalfree approach for C-C bond formation from inert C-H bonds. The reaction tolerates a wide range of aromatic rings with diverse substitution patterns, as well as terminal and internal alkenes, and is also compatible with alkynes for C-H vinylation of electron-rich arenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jian-Xin Zhang, Wei Shu
Summary: A Ni-catalyzed reductive 1,2-dialkylation reaction of unactivated aliphatic alkenes using two different alkyl bromides has been developed. The reaction proceeds smoothly under mild conditions, allowing the installation of two C-sp3-C-sp3 bonds onto directed aliphatic alkenes with excellent chemo- and regioselectivity and good functional group tolerance.
Article
Chemistry, Multidisciplinary
Wen-Tao Zhao, Huan Meng, Jia-Ni Lin, Wei Shu
Summary: In this study, a ligand-controlled regiodivergent alkylation of alkyl bromides at different positions has been developed via Ni-catalyzed alkyl-alkyl cross-electrophile coupling with a second alkyl bromide. The reaction selectively isomerizes one alkyl bromide in a controlled manner, providing diverse alkylated structures at different sites. The reaction exhibits excellent chemo- and regioselectivity at three similar positions, showcasing the remarkable ligand-tuned reactivity between alkyl-alkyl cross-coupling and nickel migration. This reaction offers a catalytic platform for the synthesis of diverse saturated architectures from identical starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Wen-Tao Zhao, Jian-Xin Zhang, Bi-Hong Chen, Wei Shu
Summary: This study reports an enantio-selective alkyl-alkyl cross-coupling reaction using a newly-developed chiral tridentate ligand. Two different alkyl halides were successfully cross-coupled to form α-tertiary aliphatic amides. The mechanism investigation revealed that one alkyl halide undergoes oxidative addition with nickel, while the other alkyl halide forms alkyl zinc reagents in situ, enabling reductive alkyl-alkyl cross-coupling without preformation of organometallic reagents.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Hai-Wu Du, Yi-Dan Du, Xian-Wang Zeng, Wei Shu
Summary: In this study, a photocatalytic synthesis of trifluoromethyl ketones from alkyl bromides and trifluoroacetic anhydride was reported. The reaction involved dual visible-light and halogen atom-transfer catalysis, followed by a radical-radical cross-coupling between an alkyl radical and a stabilized trifluoromethyl radical. This method provides a straightforward access to aliphatic trifluoromethyl ketones from readily available and cost-effective starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Yi-Dan Du, Shan Wang, Hai-Wu Du, Xiao-Yong Chang, Xiao-Yi Chen, Yu-Long Li, Wei Shu
Summary: In this study, an organophotocatalytic strategy was developed for the one-step synthesis of diverse 2-piperidinones. This mild and efficient protocol exhibits exclusive chemoselectivity and broad substrate tolerance.
NATURE COMMUNICATIONS
(2023)
Article
Multidisciplinary Sciences
Wen-Tao Zhao, Wei Shu
Summary: We report a reaction mode for the enantioselective construction of alkyl-alkyl bond to access saturated stereogenic carbon centers by asymmetric reductive cross-coupling between different alkyl electrophiles in good yields with great levels of enantioselectivity. This reaction mode uses only alkyl electrophiles for enantioselective C-sp3-C-sp3 bond-formation, rendering reductive alkyl-alkyl cross-coupling as an alternative to traditional alkyl-alkyl cross-coupling reactions between alkyl nucleophiles and alkyl electrophiles to access saturated stereogenic carbon centers without the use of organometallic reagents. The reaction displays a broad scope for two alkyl electrophiles with good functional group tolerance. Mechanistic studies reveal that the reaction undergoes a single electron transfer that enabled the reductive coupling pathway to form the alkyl-alkyl bond.
Article
Chemistry, Multidisciplinary
Jian Luo, Ai-Qing Zhong, Jia-Hao Qiu, Xiong-Wei Liu, You-Ping Tian, Bao-Hua Zhang, Guo-Shu Chen, Wei Shu, Yun-Lin Liu
Summary: A green and environmentally friendly synthetic approach has been developed for the preparation of racemic or enantioenriched 3,4,6-trisubstituted α-pyrones through a cheap K2CO3-catalyzed C(CO)-C bond insertion reaction of ketenimines with 1,3-diketones. The synthetic utility of this methodology was demonstrated by the broad substrate scope and the concise synthesis of analogues of pharmaceutically active compounds. Furthermore, the study also revealed the potential of extended conjugated α-pyrones for optoelectronic applications in organic light-emitting diodes.
Proceedings Paper
Computer Science, Artificial Intelligence
Puning Yang, Huaibo Huang, Zhiyong Wang, Aijing Yu, Ran He
Summary: In this paper, a novel contrastive distillation calibration (CDC) framework is proposed to address the issue of model generalization in face forgery detection. The framework distills contrastive representations with confidence calibration. A dual-teacher module is devised to separately learn knowledge for each forgery type, and a contrastive representation learning strategy is presented to enhance diverse forgery artifacts. Moreover, label smoothing is introduced to calibrate the model confidence with the target outputs.
COMPUTER VISION - ACCV 2022, PT IV
(2023)
Article
Chemistry, Physical
Peng-Fei Yang, Wei Shu
Summary: Stereogenic carbon centers with C(sp3)-C(sp3) bonds are widely present in natural products, bioactive targets, and chiral organic materials. Transition-metal-catalyzed C(sp3)-C(sp3) bond-forming processes offer a promising solution to generate such stereogenic centers. Recent progress in the in situ formation of alkyl metallic reagents enabled by hydrometallation of olefins for asymmetric alkyl-alkyl cross-coupling is highlighted. Mechanistic considerations, challenges, and future efforts in asymmetric hydroalkylation of olefins are also discussed.
Review
Chemistry, Multidisciplinary
Huan Meng, Ming-Shang Liu, Wei Shu
Summary: Organothianthrenium salts are compounds containing a positively charged sulfur atom and a neutral sulfur atom. They have unique structural characteristics and chemical behaviors, making them attractive precursors for forming new C-C and C-X bonds. The thianthrenation strategy allows selective transformation of C-H, C-O, and other chemical bonds into organothianthrenium salts, providing a straightforward alternative for functionalization of different compounds.
Article
Chemistry, Multidisciplinary
Jian-Xin Zhang, Peng-Fei Yang, Wei Shu
Summary: This study presents a straightforward protocol to build allylic dialkylated stereogenic centers by nickel-catalyzed regio- and enantioselective hydrovinylation. The reaction allows for the efficient construction of dialkylated allylic species in good yields with excellent enantioselectivities. It works for various alkenes and under mild conditions.
Article
Chemistry, Multidisciplinary
Yi-Zhou Zhan, Huan Meng, Wei Shu
Summary: In this study, we report a simple and practical method for the alkylalation of alkenes using a nickel catalyst. Two different alkyl bromides were used as substrates to obtain alkenes with two aliphatic substituents at room temperature.
