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Towards the total synthesis of mandelalide B: construction of the tetrahydrofuran/α-hydroxyl lactone fragment

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Org. Chem. Front., 2024, 11,6353-6357
DOI: 10.1039/D4QO01433B, Research Article
Jia-Lei Yan, Jie Yu, Yingying Cheng, Mingze Yang, Zhengshuang Xu, Tao Ye
A stereocontrolled synthesis of the tetrahydrofuran/α-hydroxy lactone fragment of mandelalide B has been accomplished. The synthesis features a Horner-Wadsworth-Emmons fragment assembly strategy and a highly stereospecific iodine-induced cyclization.
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Total synthesis of spiro Ganoderma meroterpenoids spiroapplanatumines B, D, F, and H

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Org. Chem. Front., 2024, 11,6333-6339
DOI: 10.1039/D4QO01147C, Research Article
Jia-Hao Zhang, Wen-Cai Luo, Wen-Tao Chen, Yu-Tao He, Ya-Jian Hu
The first total synthesis of spiroapplanatumines B, D, F, and H as well as the possibly undiscovered natural product spiroapplanatumine R has been achieved.
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Visible-light excited copper activating unactivated alkyl iodides for radical addition/cyclization to access oxindole derivatives

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Org. Chem. Front., 2024, 11,6380-6384
DOI: 10.1039/D4QO01329H, Research Article
Hang Luo, Fangnian Yu, Luqing Lin
The photocopper catalyst facilitates halogen atom transfer to give unactivated alkyl radicals, which is critical for achieving radical cyclization in the absence of an exogenous photocatalyst.
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Iridium/palladium dual photocatalysis for oxidative decarboxylative esterification of alcohols using α-keto acids

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Org. Chem. Front., 2024, 11,6367-6379
DOI: 10.1039/D4QO01452A, Research Article
Subal Mondal, Soumya Mondal, Debabrata Halder, Siba P. Midya, Ankan Paul, Pradyut Ghosh
Herein, we report an unprecedented oxidative decarboxylative C–O cross-coupling reaction for the esterification of feedstock α-keto carboxylic acids and alcohols under mild conditions.
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Transition-metal-catalyzed regiodivergent sulfonylation of aziridrines for the synthesis of β-amino sulfones

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Org. Chem. Front., 2024, 11,6340-6346
DOI: 10.1039/D4QO01376J, Research Article
Qinqiong Zeng, Yujia Gong, Xiaochun He, Xuemei Zhang, Zhong Lian
We developed the first transition-metal-catalyzed, regiodivergent sulfonylation of aziridines, enabling the efficient synthesis of diverse β-amino sulfones under mild conditions with broad substrate compatibility and high regioselectivity.
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A cucurbit[8]uril-mediated host–guest complex for red-light photocatalysis

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Org. Chem. Front., 2024, 11,6327-6332
DOI: 10.1039/D4QO01492H, Research Article
Weiquan Xu, Yinghao Du, He Ma, Xingchen Tang, Jiang-Fei Xu, Xi Zhang
Two-step host–guest complexation can occur between an elongated dye and CB[8], leading to the formation of CB[8]@2TPP and 3CB[8]@2TPP sequentially. Of these species, 3CB[8]@2TPP in particular can act as an efficient red-light photocatalyst.
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Visible light-induced aerobic photooxidative cleavage of C(sp3)–C(sp2) σ-bonds of allylarenes

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Org. Chem. Front., 2024, 11,6385-6392
DOI: 10.1039/D4QO01243G, Research Article
Jinyu Tang, Xi Zhao, Jinxuan Ni, Yanping Huo, Yang Gao, Xianwei Li, Yan Liu, Keiji Maruoka, Qian Chen
A cleavage of C(sp3)–C(sp2) σ-bonds of allylarenes to aromatic aldehydes and ketones has been achieved via a visible light-induced photocatalysis.
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Asymmetric synthesis of (aza)flavanones by the evolution of CarOx ligands

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Org. Chem. Front., 2024, 11,6444-6449
DOI: 10.1039/D4QO01345J, Research Article
Juan Yang, Wenlong Kong, Mingxin Chang, Jixing Lai, Shengkun Li
Amino-pyridine-oxazoline (NHPyOx) is conceived as an unprecedented model via the core-emulating optimization of CarOx ligands.
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Theoretical insights into Pd-catalyzed dual γ-1,1-C(sp3)–H activation of aliphatic carboxylic acids: mechanistic pathways, substituent influence on product selectivity, diastereoselectivity, and additive effects

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Org. Chem. Front., 2024, 11,6393-6410
DOI: 10.1039/D4QO01451K, Research Article
Jiaoyang Liu, Li-juan Huang, Zeang Sun, Juan Li
DFT calculations were employed to explore the detailed reaction mechanism and the origins of the experimentally observed product, regio-, and diastereoselectivities in the Pd-catalyzed dual-γ-1,1-C(sp3)–H activation of aliphatic carboxylic acids.
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Design, synthesis and application of bipyridine-N,N'-dioxide catalysts in asymmetric synthesis of chiral cyclopropanes

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Org. Chem. Front., 2024, 11,6470-6476
DOI: 10.1039/D4QO01532K, Research Article
Xiaoying Cao, Xue Tian, Minmin Liu, Shi-Wu Li
A novel type of highly efficient chiral C2-symmetric bipyridine-N,N'-dioxide ligands was prepared and successfully applied in the synthesis of optically pure 1,2,3-trisubstituted cyclopropanes.
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A general method for E-selective olefination of acylsilanes with isocyanides via silver catalysis

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Org. Chem. Front., 2024, 11,6450-6458
DOI: 10.1039/D4QO01528B, Research Article
Xiu-Xia Liang, Dan-Ni Yang, Xiao-Hui Yan, Peng Wang, Man-Yi Han
A silver-catalyzed olefination reaction between acylsilanes and isocyanides is developed, resulting in E-vinylsilanes with good yields and high stereoselectivities.
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Visible-light-promoted catalytic epoxidation of alkenes under metal-free conditions

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Org. Chem. Front., 2024, 11,6437-6443
DOI: 10.1039/D4QO01265H, Research Article
Dabao Tan, Xiaoyan Cai, Lele Zhang, Boyu Liu, Jianbin Zeng, Feiming Li, Zhixiong Cai, Mingqiang Huang, Xiaoping Chen, Shunyou Cai
In this work, we report a method for the synthesis of functionalized epoxy analogues using the synergistic interaction of 4CzIPN and oxygen under visible light stimulation.
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Activation of donor–acceptor cyclopropanes under basic conditions: ring opening of 2-(p-siloxyaryl)cyclopropane 1,1-dicarboxylates with nitro compounds and other C-nucleophiles

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Org. Chem. Front., 2024, 11,6483-6494
DOI: 10.1039/D4QO01472C, Research Article
Yulia A. Antonova, Andrey A. Tabolin
A new activation mode for donor–acceptor cyclopropanes was proposed and implemented in their reaction with nitro compounds and other common C-nucleophiles.
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Carbonate-assisted selectively deoxygenative cross-coupling reaction between aryl and aliphatic aldehydes: a straightforward route to access α-alkylated aryl ketones

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Org. Chem. Front., 2024, 11,6510-6517
DOI: 10.1039/D4QO01517G, Research Article
Yu Sun, Yi Wang, Zhijun Zuo
A novel reductive cross-coupling reaction of two different aldehydes for rapidly assembling α-alkylated aryl ketones has been developed. The inexpensive carbonate served not only as a base but also as an efficient electron donor.
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Anomalous magnetic behaviour induced by a structural phase transition with anisotropic thermal expansion in a spirodiradical

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Org. Chem. Front., 2024, 11,6495-6502
DOI: 10.1039/D4QO01098A, Research Article
Open Access
Takuya Kanetomo, Daigo Matsunaga, Shinichi Ogawa, Masaya Enomoto
A Ge-centred spirodiradical exhibited anomalous magnetic behaviour, influenced by two key structural factors: negative thermal expansion and a structural phase transition.
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Sulfenylation of bioactive maleimides, acrylates and cyclohexenones under ambient organophotocatalysis

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Org. Chem. Front., 2024, 11,6503-6509
DOI: 10.1039/D4QO01342E, Research Article
Debanjana Bag, Rajjakfur Rahaman, Anindya S. Manna, Subhasis Pal, Rajesh Nandi, Shobhon Aich, Narendra Nath Ghosh, Dilip K. Maiti
A novel visible light-induced sulfenylation of biologically important maleimides, acrylates and cyclohexenones has been developed using cheap and easily available organophotoredox catalyst Eosin Y with thiols under ambient conditions.
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Transition-metal-catalyzed C–Ge coupling reactions

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Org. Chem. Front., 2024, 11,6558-6572
DOI: 10.1039/D4QO01637H, Review Article
Jie Ke, Cadmus Du Chen, Li-Qing Ren, Bing Zu, Bin Li, Chuan He
This review covers the development and recent progress in transition-metal-catalyzed C–Ge coupling reactions. The goal is to provide a clear overview of the field, identify current challenges, and inspire further applications in this growing area.
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Shining light on sulfonium salts and sulfur ylides: recent advances in alkylation under photoredox catalysis

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Org. Chem. Front., 2024, 11,6573-6588
DOI: 10.1039/D4QO01644K, Review Article
Zhe Jin, Tingwei Yu, Hui Wang, Penghao Jia, You Huang
Recent advancements in photoredox alkylation with sulfur ylides, sulfonium salts and related analogues are summarized in this review.
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Recent advances in asymmetric synthesis of chiral benzoheterocycles via Earth-abundant metal catalysis

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Org. Chem. Front., 2024, 11,6534-6557
DOI: 10.1039/D4QO01686F, Review Article
Jinhui Cai, Wenting Zhang, Usman Muhammad, Weishuang Li, Yanjun Xie
This review mainly focus on the assembly of chiral benzoheterocycles, such as dihydrobenzofurans, chromans, indolines, tetrahydroquinolines, etc., via Earth-abundant metal-catalyzed (Cu, Fe, Ni, and Ti) asymmetric synthesis in the last few decades.
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A two-step Kinugasa/Conia-ene-type sequential reaction for the asymmetric synthesis of 8-methylene-2,6-diazaspiro[3.4]octane-1,5-diones

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01388C, Research Article
Shanyue Li, Qicai Ma, Bohua Wu, Haowen Ma, Wei Zhou, Qian Cai
A two-step Kinugasa/Conia-ene-type sequential reaction is developed. The process provided a simple and efficient access to chiral 8-methylene-2,6-diazaspiro[3.4]octane-1,5-diones.
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DABSO-Mediated Pummerer Reaction Enables One-Pot Synthesis of Pyrroloquinolines for Accessing Marinoquinolines: Mechanistic, Photophysical and Pharmacological Investigations

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO01512F, Research Article
Rahimuddin Khan, Dipun Kumar Penthi, Aditi Chatterjee, Chandrakanta Sahoo, Shanti Gopal Patra, Viswanathan Arun Nagaraj, Tabrez Khan
A new one-pot acid- and exogenous oxidant-free synthesis of pyrrolo[2,3-c]quinolines has been developed. The strategy involves chemoselective reduction of the 3-(2-nitrophenyl)-1H-pyrroles (pyrrolnitrin derivatives) and subsequent DABSO-facilitated Pummerer reaction in the...
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Charge Transfer Complex Enabled Mechanochemical Synthesis of Chalcogenoacetylenes via Alkynyl Radicals

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO01827C, Research Article
Open Access
Fang Tan, Chang-Zhen Fang, Bing-Sheng Qiu, He Sheng, Yong-Liang Tu, Xiang-Yu Chen
Mechanochemistry has become an appealing strategy to enable numerous organic transformations. While significant advances have been achieved, the radical coupling reaction under mechanochemical conditions is still in its infancy. In...
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Copper(II)-catalyzed synthesis of sulfonyl-functionalized quinone-fused cyclopenta[b]indoles via four-component cascade annulation

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01560F, Research Article
Hong Xu, Jie Liao, Fei Ren, Chuan-Rong Zhou, Xiao-Zhuo Liu, Yao Xiao, Dong-Wei Hang, Fuyu Li, Bei Wang, Ji-Yu Wang
Through crucial selective radical tandem process and intramolecular nucleophilic addition, a facile copper-catalyzed four-component cascade has been realized to selectively construct novel sulfonyl-functionalized quinone-fused cyclopenta[b]indole.
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Facile single-step synthesis of pentaaryl-substituted pyrano[3,2-b]pyrrol-5(1H)-ones showing aggregation-induced emission

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01600A, Research Article
Yongfeng Wang, Ruijun Chu, Yanxiao Wang, Mengyuan Zhou, Yuan Chen, Cheng Xu, Jingyu Sun, Guodong Yin
A novel class of heterocyclic AIEgens has been synthesized via a multicomponent reaction of isatins, 2,3-diaryl cyclopropenones, and alkyl bromides.
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Recent advances in carbon atom addition for ring-expanding single-atom skeletal editing

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01806K, Review Article
Ting Yuan, Lei Shi
This review focuses on recent advances in carbon atom addition for ring-expanding single-atom skeletal editing.
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Catalytic asymmetric synthesis of chiral sulfilimines via S-C bond formation

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO01963F, Highlight
Yingying Shi, Shuiyun Zheng, Jiapian Huang, Fu-Sheng He, Min Yang, Jie Wu
As the aza-analogues of sulfoxides, sulfilimines bearing S(IV) stereogenic centers hold tremendous potential in synthetic chemistry and medicinal chemistry. However, the catalytic asymmetric synthesis of chiral sulfilimines are much less...
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Thiocyanoalkylation of Alkenes via Dual Photoredox and Copper Catalysis

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO01864H, Research Article
Xu Wang, Bi-Yin Xiao, Qi-Xuan Jiang, Wei Huang, Feng-Hua Zhang
Organic thiocyanates are commonly used as an essential organic synthesis intermediate and widely present in various drug molecules and bioactive molecules. Herein, a copper and photoredox catalyzed thiocyanoalkylation reaction of...
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Stereocontrolled synthesis of heterocycles from unactivated alkynes by photoredox/nickel dual-catalyzed cyclization

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01627K, Research Article
Bo-Rong Leng, Feng Yang, Jin-Lian Bai, Yu-Wen Huang, Qing-Quan Liu, Ping Wei, De-Cai Wang, Yi-Long Zhu
We report a nickel/photoredox dual catalysis method for synthesizing heterocyclics from unactivated alkynes and aryl iodides, offering a direct, selective, and green alternative to traditional synthesis with potential in medicinal chemistry.
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Integrating electrocatalysis with biocatalysis for asymmetric synthesis

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01899K, Highlight
Yuqi Lin, Jiage Yu, Ke-Yin Ye
This highlight presents recent advances in asymmetric synthesis that integrate electrocatalysis with biocatalysis and discusses future development directions in this field.
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Probing Intersystem Crossing in Multi-brominated Eumelanin through Transient Absorption and Surface Hopping Dynamics

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO01832J, Research Article
Open Access
Kavya Vinod, Lukhmanul Hakeem K., Diana Thomas, Pallavi Panthakkal Das, Mahesh Hariharan
Achieving intersystem crossing (ISC) through structural tuning in biological systems is an evolving area for therapeutic and materials research. Eumelanin, a natural pigment, offers huge potential for bio-inspired material design,...
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Magic effect of diphenylprolinol silyl ether for the enantioselective allenation of 2-alkynals

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00984C, Research Article
Guolin Wu, Zhen Liu, Shiwen Fan, Wenyao Li, Xue Zhang, Hui Qian, Shengming Ma
Chiral diphenylprolinol silyl ethers have been successfully identified for the enantioselective allenation reaction of terminal alkynes and 2-alkynals, delivering a diverse set of chiral allenynes with high efficiency.
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Visible-light responsive defluorination-acyl fluoride exchange for photoclick labeling based on phenoxazine chromophores

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01870B, Research Article
Lijun Deng, Sitong Li, Cefei Zhang, Yuqiao Zhou, Zhishan Su, Changwei Hu, Xiaohu Zhao, Zhipeng Yu
We developed a new generation of photo-DAFEx reagents to realize photoaffinity labeling for drug discovery under 405 nm light control.
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Metal–ligand cooperation and synergistic palladium catalysis for the dual ligand system [2,2'-bipyridin]-6(1H)–one/PCy3: milder conditions for the undirected C–H arylation of arenes

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01877J, Research Article
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Cintya Pinilla, Mario García-Zarza, Ana C. Albéniz
The mixture of Pd(OAc)2 and two ligands segregate into distinct active species working synergistically for the C–H arylation of simple arenes.
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Palladium-catalyzed cascade decarboxylative cyclization of alkyne-tethered aryl iodides with o-bromobenzoic acids for the synthesis of fused isoquinolinones

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01573H, Research Article
Zhaolin Quan, Yubo Duan, Zhengkai Chen
A straightforward approach for the preparation of fused isoquinolinone derivatives via palladium-catalyzed cascade decarboxylative cyclization of alkyne-tethered aryl iodides with o-bromobenzoic acids is described.
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Synthesis of oxa-bridged carbocycles via rhodium/Lewis acid catalyzed [3 + 3] and [4 + 3] cycloadditions of carbonyl ylides with donor–acceptor strained carbocycles

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01831A, Research Article
Jiale Li, Lingfei Wang, Pei-Nian Liu, Xingguang Li
A method for cooperative rhodium/Lewis acid-catalyzed cycloadditions of carbonyl ylides with donor–acceptor (D–A) strained carbocycles is described. It affords structurally diverse oxa-bridged carbocycles with high efficiency and stereoselectivity.
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Transition-metal-free skeletal editing of benzoisothiazol-3-ones to 2,3-dihydrobenzothiazin-4-ones via single-carbon insertion

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01714E, Research Article
Ke Yang, Qin Li, Yanqi Luo, Dan Yuan, Chunjian Qi, Zhengyi Li, Bijin Li, Xiaoqiang Sun
Transition-metal-free ring expansion of benzoisothiazol-3-ones has been established to construct various 2,3-dihydrobenzothiazin-4-ones via single-carbon insertion.
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Rh-Catalysed Hydroacyloxylation of Cyclopropenes: Regio- and Diastereoselective Synthesis of Acyloxycyclopropanes

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO01810A, Research Article
Ángel Manu Martínez, Gema Domínguez, Ines Alonso, Marta Palaín, Javier Perez-Castells
Cyclopropyl carboxylates are essential building blocks in biological and medicinal chemistry. However, their accessibility is severely limited by the need to pre-synthesise highly reactive cyclopropane derivatives. Herein, we report an...
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PIFA-Mediated cyclization of methyl(2-(1-phenylvinyl)phenyl)sulfane for the concise, flexible, and scalable de novo synthesis of C3-arylated benzo[b]thiophenes

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO01589D, Research Article
Xinya Liu, Olivier Provot, Christine Tran, Jean-Francois Soule, Abdallah Hamze
The well-decorated arylated benzo[b]thiophene scaffold is a pivotal structural motif with diverse applications in medicinal chemistry. This paper outlines a de novo synthesis of C3-arylated benzo[b]thiophenes, showcasing its flexibility and...
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Hemilabile P,N-Ligand-Assisted Gold Catalyzed Hiyama Allylation to Access Allylarenes and 1,4-Dienes Derivatives

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Org. Chem. Front., 2025, Accepted Manuscript
DOI: 10.1039/D4QO01879F, Research Article
Yuanhao He, Wanping Ma, Yu Zhong, Yanfei Hu, Mingou Li, Fen Zhao, Zhonghua Xia, Baomin Fan
Oxidant-free gold-catalyzed reactions are emerging as a novel synthetic tool for organic transformations. Here in, we reported a hemilabile P,N-ligand-assisted gold-catalyzed Hiyama cross coupling reaction of aryl and alkenyl iodides...
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Rhodium-catalyzed synthesis of N-substituted 3-acylpyrroles from enaminones and vinylene carbonate

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Org. Chem. Front., 2025, Accepted Manuscript
DOI: 10.1039/D4QO01816H, Research Article
Sheng-Jiao Yan, Jian-Bo Ma, Yi-Mai Yin, Xing-Mei Hu, Bi-Na Shao, Kun Huang, Qing-Sheng Zhao
Skeletal editing is a highly efficient strategy for modifying the core scaffolds of drug molecules, with multi-atomic editing as an emergent approach. Herein, we present a protocol for constructing N-substituted...
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π-extended regioisomeric dithienoacenes fused pyrenes: structures, properties, and application in field-effect transistors

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Org. Chem. Front., 2025, Accepted Manuscript
DOI: 10.1039/D4QO01592D, Research Article
Bin Lu, Shiqian Zhang, Dong Liu, Wendong Jin, Dalin Li, Zhiqiang Liu, Tao He
The development of π-conjugated semiconducting molecules with fused rings has been a focus of research in organic electronics. In this study, optoelectronic and field-effect transistors (FET) properties of two novel...
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Mechanistic insights into rhodium-catalyzed C−H activation and annulation using vinyl acetate to access cinnolines and cinnolin-4(1H)-ones

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Org. Chem. Front., 2025, Accepted Manuscript
DOI: 10.1039/D4QO01734J, Research Article
Yuqin Wang, Yiling Zeng, Ya-Nan Tian, Zheng Liu, Jinhua Wang, Shuyou Chen, Shiqing Li
Transition metal-catalyzed C−H activation and annulation involving vinyl acetate remains a significant challenge, and the mechanistic process following vinyl insertion is ambiguous. Herein, we report the Rh(III)-catalyzed two-fold C−H activation...
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Intermolecular Defluorinative 1,2-Diamination of Fluoroalkenyl Iodides with Sulfonamides: Synthesis of Acyclic and Cyclic Fluorinated 1,2-Enediamines

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Org. Chem. Front., 2025, Accepted Manuscript
DOI: 10.1039/D4QO01913J, Research Article
Xue-Qiang Chu, Yu-Lan Chen, Chi Zhang, Xue-Ying Huang, Yu Ding, Danhua Ge, Zhi-Liang Shen
Alkene diamination represents one of the most straightforward strategies for 1,2-diamine derivatives synthesis. However, transition-metal-free 1,2-diamination of fluoroalkenes has been less studied. Here we report an intermolecular defluorinative vicinal diamination...
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