Article
Chemistry, Physical
Bo-Han Zhu, Ying-Qi Zhang, Hao-Jin Xu, Long Li, Guo-Cheng Deng, Peng-Cheng Qian, Chao Deng, Long-Wu Ye
Summary: An efficient copper-catalyzed tandem alkyne hydration/intramolecular Mannich reaction has been investigated for the synthesis of valuable compounds. This method allows the efficient synthesis of 3,4-dihydro-2-quinolones with high regio-, diastereo-, and enantioselectivity.
Article
Chemistry, Multidisciplinary
Nengneng Zhou, Qiankun Xu, Ziqin Xia, Kaimo Kuang, Sixin Wu, Wenping Li, Man Zhang
Summary: In this study, a novel palladium-catalyzed radical cascade reaction was developed for the synthesis of cyanoalkylsulfone-containing cyclopenta[gh]phenanthridines. The reaction involved the cleavage of a C-C single bond and insertion of SO2, and showed mild reaction conditions, a broad substrate scope, and high functional group tolerance.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Yin Xu, Gan-Lu Qian, Da-Qiu Cui, Peng-Cheng Qian, Chao-Yue Zhao, Xin Hong, Bo Zhou, Long-Wu Ye
Summary: Herein, a chiral Bronsted acid-catalyzed desymmetrization reaction of diynes is reported, providing a facile access to enantioenriched 1,3-diaminopropanol derivatives and γ-butyrolactones with high enantioselectivities. These products can be used as precursors for the synthesis of versatile N- and O-heterocycles, which are important structural cores of bioactive molecules. Control experiments and theoretical calculations are used to confirm the mechanism and elucidate the origin of enantioinduction.
Article
Chemistry, Physical
Lin-Jun Qi, Chong-Yang Shi, Peng-Fei Chen, Long Li, Gang Fang, Peng-Cheng Qian, Chao Deng, Jin-Mei Zhou, Long-Wu Ye
Summary: The study presents a novel gold-catalyzed 1,1-carboalkoxylation method for the synthesis of valuable cyclic compounds, enabling asymmetric synthesis through a chirality-transfer strategy. Further mechanistic insight into the distinct migration into gold carbenes is supported by theoretical calculations.
Article
Chemistry, Multidisciplinary
Shangbiao Zhang, Yan Gao, Rui Xiao, Yang Li, Yanan Wang, Zheliang Yuan
Summary: In this study, a tandem synthesis of various CF3Se-containing heterocyclic compounds was developed using Tf2O as the catalyst and trifluoromethyl selenoxides as the electrophilic trifluoromethylselenolation reagents. The process is characterized by its mild conditions, easy operation, and good functional group compatibility. A variety of alkynes were successfully transformed into CF3Se-containing indoles, benzofurans, benzothiophenes, isoquinolines, and chromenes in good yields.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Jin-Chen Li, Bing-Xia Yan, Gang Wang, Zhi-Shi Ye
Summary: Here, we demonstrated an efficient cascade reaction of N-tosyl ortho-alkynylanilines and N-acyl ortho-alkynylanilines using Rh(COD)(2)BF4/( t )BuXantPhos as a catalyst. The reaction exhibited excellent chemoselectivity and regioselectivity, high atom-economy, and wide substrate scope. Mechanistic studies revealed that the success of this reaction relied on the strong capability of the rhodium catalyst to recognize the N-substituent group in the selective nucleophilic cyclization and alkyne insertion.
Article
Chemistry, Multidisciplinary
Sanghyup Seo, Donghyeon Kim, Hyunwoo Kim
Summary: The reductive cross-coupling of terminal alkenes and N-heterocyclic bromides was successfully demonstrated through ligand optimization of Pd and CuH catalysis. The optimized ligands for Pd and CuH catalysis, Briphos and DTB-DPPBz respectively, were further applied to gram-scale production of clathryimine B.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Gilson Zeni, Benhur Godoi, Carla K. Jurinic, Andrei L. Belladona, Ricardo F. Schumacher
Summary: This manuscript provides an overview of the most recent advances in the synthesis of carbo- and heterocycles through reactions of alkynes with organyl chalcogenides under metal-free conditions. Methods discussed include the use of electrophilic chalcogenyl halides and radical cyclization protocols utilizing electrochemical oxidative conditions, light-induced photoredox catalysis, or mild oxidants.
Article
Chemistry, Organic
Leilei Cao, Liliang Huang, Xianjun Xu, Erik V. Van der Eycken, Huangdi Feng
Summary: A novel method for the construction of nitrogen-tethered 1,6-enynes with high atom economy and exclusive chemoselectivity has been developed. Experimental studies suggest that the key step in this methodology is the alkyne-iminium ene reaction involving an intermolecular hydride transfer.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Guang-Yu Zhu, Ji-Jia Zhou, Li-Gao Liu, Xiao Li, Xin-Qi Zhu, Xin Lu, Jin-Mei Zhou, Long-Wu Ye
Summary: A catalyst-dependent [3,3]-sigmatropic rearrangement of sulfoxide-ynamides has been described, enabling the divergent and atom-economic synthesis of valuable medium-sized N,S-heterocycles with moderate to good yields and broad substrate scope. Excellent enantioselectivities have been achieved via an unprecedented chirality-transfer. Theoretical calculations have been employed to elucidate the origins of the catalyst-dependent stereospecific [3,3]-rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Angelica R. Claus, Tales A. C. Goulart, Davi F. Back, Gilson Zeni
Summary: In this study, a regio- and stereoselective synthesis of alpha-methylene-beta-lactams was reported via a 4-exo-dig-cyclization of N-benzyl-N-methyl-propiolamides catalyzed by a base. Experimental evidence suggests that the transformation proceeds through a concerted ionic cyclization, followed by protonation of the vinyl species promoted by tert-butanol. The obtained alpha-methylene-beta-lactams were suitable substrates for the Heck coupling conditions, leading to the formation of corresponding products through carbon-carbon bond formation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Marina Yu. Dvorko, Dmitrii A. Shabalin, Igor A. Ushakov, Elena Yu. Schmidt, Boris A. Trofimov
Summary: The cascade dimerization of alkynones with sterically hindered secondary alkyl groups at the carbonyl function unexpectedly produced highly functionalized furans. This reaction efficiently takes place at room temperature in the presence of a potassium tert-butoxide/dimethylsulfoxide superbase catalytic system. Alkynones with an additional C-H active site at the carbon-carbon triple bond followed a different dimerization pathway to form 3-alkenylpyran-4-ones. The discovery of these reactions expands the traditional understanding of alkynone reactivity in strong basic conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shuai Jiang, Wen-Bin Cao, Xiao-Ping Xu, Shun-Jun Ji
Summary: A Co-catalyzed cyclization reaction of isocyanides, azides, and amines was developed to access quinazoline derivatives, featuring high atom economy, mild reaction conditions, excellent yields, and a broad substrate scope. The cascade reaction involved the formation of three to four C-N bonds and one or two rings, producing versatile intermediates for further transformations. The cobalt catalyst used in the reaction was found to be isolatable and reusable.
Article
Multidisciplinary Sciences
Benxiang Zhang, Jiayan He, Yang Gao, Laura Levy, Martins S. Oderinde, Maximilian D. Palkowitz, T. G. Murali Dhar, Michael D. Mandler, Michael R. Collins, Daniel C. Schmitt, Philippe N. Bolduc, Teyu Chen, Sebastian Clementson, Nadia Nasser Petersen, Gabriele Laudadio, Cheng Bi, Yu Kawamata, Phil S. Baran
Summary: Modern retrosynthetic analysis in organic chemistry is a method that guides the design of synthetic routes based on the polar relationships between functional groups. This approach assigns charges to functional groups and disconnects bonds between them. It has applications in undergraduate curriculum and synthetic methods, but requires careful considerations to overcome selectivity and oxidation state issues. In this study, a radical-based Ni/Ag-electrocatalytic cross-coupling of substituted carboxylic acids was reported, enabling a simplified approach to accessing complex molecular architectures.
Article
Chemistry, Organic
Fang Wang, Qianting Zhou, Xinying Zhang, Xuesen Fan
Summary: A novel and efficient alpha-C(sp(3))-H alkenylation of cyclic amines with maleimides was presented, featuring readily available and structurally diverse substrates, a green and economical catalyst, a unique reaction pathway, mild reaction conditions, high efficiency, and excellent atom economy. This new reaction enriches the application of Fe(III)-catalyzed C(sp(3))-H activation and functionalization.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Shigeru Arai, Masaya Nakajima, Atsushi Nishida
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2018)
Article
Chemistry, Organic
Shigeru Arai, Koki Matsumoto, Atsushi Nishida
Article
Chemistry, Organic
Shigeru Arai, Koichi Nakazawa, Xiao-fei Yang, Atsushi Nishida
Review
Chemistry, Medicinal
Shigeru Arai
CHEMICAL & PHARMACEUTICAL BULLETIN
(2019)
Review
Chemistry, Organic
Shigeru Arai, Yuka Amako, Hiroto Hori, Atsushi Nishida
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2019)
Article
Chemistry, Applied
Shigeru Arai, Arisa Izaki, Yuka Amako, Masaya Nakajima, Masanobu Uchiyama, Atsushi Nishida
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Organic
Shigeru Arai, Yuna Kawata, Yuka Amako, Atsushi Nishida
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Multidisciplinary
Shinji Harada, Saki Nakashima, Shihori Sekino, Wakana Oishi, Atsushi Nishida
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Organic
Shigeru Arai, Yuichi Sato, Natsuki Ito, Atsushi Nishida
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Yuna Kawata, Shigeru Arai, Masaya Nakajima, Atsushi Nishida
Summary: The highly regio- and stereoselective homodimerizative [2 + 2] cycloaddition of allenamides under nickel catalysis was investigated, with Xantphos ligand playing a crucial role in product formation. DFT studies revealed that oxidative addition is a key process, leading to the formation of cyclobutane as a single isomer in a sequential manner.
TETRAHEDRON LETTERS
(2021)
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, Organic
Hiroto Hori, Shigeru Arai, Atsushi Nishida
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
