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Base- and metal-free visible-light driven site-selective α-C(sp3)–H functionalization reaction of glycine derivatives with hydroxamic acid derivatives Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-17 Shiyun He, Hongying Fan, Xue Zhang, Meiling Ye, Jian Chen, Jinyu Hou, Tianle Huang, Li Guo, Guanghui Lv, Yong Wu
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Copper-catalyzed oxidative sulfenylation and alkylation of indolin-2-ones for direct construction of sulfur-substituted quaternary carbons Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-12 Yun-Hao Zhang, Yi-Nuo Wang, Zi-Yu Liu, Si-Han Zheng, Guang-Lin Li, Dexin Feng, Da-Zhen Xu
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Metal-free photoinduced denitrogenative alkylation of vinyl azides with alkyl radicals toward ketones Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-12 Hui Yin, Siqi Jian, Xiujuan Feng, Ming Bao, Xuan Zhang
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Aculeatones A and B, epimeric lovastatin derivatives with a 6/6/3-tricyclic carbon skeleton from Aspergillus aculeatus and their chemical transformation Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-11 Fei Liu, Fengqing Wang, Qin Li, Bingbing Dai, Weiguang Sun, Jianguo Li, Chunmei Chen, Yonghui Zhang, Hucheng Zhu
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Visible-light-mediated catalyst-free synthesis of trifluoromethyl(spiro)-epoxides bearing contiguous quaternary centers Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-15 Jingchuan Lin, Yu Zhang, Jinxin Wang, Xinyu Han, Shenglan Zhu, Tong Li, Yanping Zhu, Wei-Dong Zhang
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Correction: Stereodivergent and enantioselective total syntheses of isochaetominines A–C and four pairs of isochaetominine C enantiomers: a six-step approach Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-15 Zhong-Yi Mao, Hui Geng, Tian-Tian Zhang, Yuan-Ping Ruan, Jian-Liang Ye, Pei-Qiang Huang
Correction for ‘Stereodivergent and enantioselective total syntheses of isochaetominines A–C and four pairs of isochaetominine C enantiomers: a six-step approach’ by Zhong-Yi Mao et al., Org. Chem. Front., 2016, 3, 24–37, https://doi.org/10.1039/C5QO00298B.
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Selective deletion of one carbon atom from C60 through benzylamine mediated reactions Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-10 Yaqiong Wang, Yiran Wu, Yuming Yu, Jie Su, Yi Qiu, Liangbing Gan
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Development of a photoenzymatic one-pot hybrid system for the direct synthesis of 3,3-disubstituted indole-2-ketones from N-methyl indoles Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-10 Yao Yao, Yuan Yu, Ming-Liang Shi, Xin-Yue Fan, Ru-De Lin, Kun Li, Wen-Dian Li, Fei-Yan Tao, Na Wang
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Organocatalytic formal [4 + 2] cycloaddition of o-quinone-methyl derivatives and 2-isocyanatomalonate diesters for the construction of chroman derivatives with adjacent quaternary chiral centers Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-09 Tong Xiong, Yi-Zhao Xu, Yao Wang, You-Cai Xiao, Fen-Er Chen
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Asymmetric [3 + 2] cycloaddition of donor–acceptor cyclopropanes with azadienes enabled by Brønsted base catalysis Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-04 Shu Li, Zhi-Hong Dong, Si-Yu Dan, Mei-Jun Zheng, Teng Long, Jie Zhan, Qing Zhou, Wen-Dao Chu, Quan-Zhong Liu
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NBN/BNB-doped phenalenyl homo- and heterodyads: structural uniformity but optoelectronic diversity Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-09 Alexander S. Scholz, Thomas Froitzheim, Michael Bolte, Hans-Wolfram Lerner, Jan-M. Mewes, Matthias Wagner
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A retro-Mannich mediated transformation of Morita–Baylis–Hillman ketones to saturated imidazo[1,2-a]pyridines Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-09 Sachin Sharma, Ajit Kumar Jha, Srinivasan Easwar
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Assembly of ionic supramolecular polymers using a decacationic pillar[5]arene to noncovalently crosslink hyaluronic acid for short DNA delivery Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-09 Qian Li, Danying Ma, Yue-Yang Liu, Hui Wang, Wei Zhou, Dan-Wei Zhang, Zhan-Ting Li
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Three-component Friedel–Crafts-type difunctionalization of ynamides with (hetero)arenes and iodine(III) electrophile Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-09 Jun Kikuchi, Toya Nagata, Shingo Ito, Naohiko Yoshikai
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Regio- and stereo-selective synthesis of β-phenylthio enamides via intramolecular 1,2-thiol migration Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-08 Yunqing Zhuang, Jin Zhang, Kai Yang, Gehua Bi, Xin Huang, Weimin Zhang
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Correction: Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-08 Junjie Ying, Jingrong Huang, Chenguang Liu, Fa-Jie Chen, Chunfa Xu, Fen-Er Chen
Correction for ‘Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids’ by Junjie Ying et al., Org. Chem. Front., 2024, 11, 53–59, https://doi.org/10.1039/D3QO01534C.
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Synthesis of a helical boron-doped PAH by post-functionalization of 3,9-diboraperylene Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-08 Carina Mützel, Kazutaka Shoyama, Ana-Maria Krause, Frank Würthner
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NHC and photoredox catalysis dual-catalyzed 1,4-mono-/di-fluoromethylative acylation of 1,3-enynes Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-08 Jiuli Xia, Ruiyang Ma, Lihong Wang, Jiaqiong Sun, Guangfan Zheng, Qian Zhang
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Cobalt-catalysed Csp3–Csp3 cross-coupling of benzyl Katritzky pyridinium salts with Callyl–O electrophiles Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-08 Mengyu Gao, Corinne Gosmini
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Sustainable synthesis of long-acting local anesthetics ropivacaine and levobupivacaine under batch and continuous flow via asymmetric hydrogenation Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-02 Zhi Yang, Hanlin Chen, Linxi Wan, Xinyi Feng, Lingshuang Ma, Pei Tang, Fen-Er Chen
Ropivacaine and levobupivacaine, long-acting local anesthetics, have been sustainably synthesized using both batch and continuous flow methods. The key reaction, iridium-catalyzed enantioselective hydrogenation of 2-alkoxycarbonyl pyridinium salts, proceeds with excellent yields and enantioselectivities, as well as mild reaction conditions under both batch and flow modes. This approach provides a direct
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Blue light-mediated carbene transfer reaction of thioesters with diazoesters: efficient synthesis of tetrasubstituted Z-enol esters Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-04 Shuncheng Wang, Hua Zhang, Jin Yang, Dongfang Zhang, Xin-Ping Hui
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Electrochemical switching in mechanically interlocked molecules (MIMs) Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-04 Ayush Bhadani, Murugavel Kathiresan
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Triazatriangulenium salts – hosts and guests in supramolecular assemblies in solution Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-04 Sayan Sarkar, Michael Böck, Agnes Uhl, Aleksandr Agafontsev, Jürgen Schatz, Evgeny A. Kataev
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Decarbonylative C(sp2)–C(sp2) reductive cross-coupling of aroyl fluorides with aryl bromides by palladium/cobalt co-catalysis Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-03 Chen He, Zhiyong Song, Wei Yao, Rui Lin, Yuanhong Ma
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Stereodivergent synthesis of chiral spiropyrazolones through Pd-catalyzed asymmetric sequential hydroalkylation of 1,3-enynes: unusual solvent effects on the enantioselectivity Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-03 Shan Wang, Long Li, Yifei Zheng, Luqing Li, Yingcheng Wang, Fangzhi Peng, Zhihui Shao
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Electrochemically dehydrogenative C(sp2)–H/S–H cross-coupling: efficient synthesis of ortho-aminophenyl thioglycoside derivatives Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-03 Li-Yan Hu, Li Zhu, Shen-Yuan Zhang, Yu-Xin Guo, Yuan Li, Jie Zhu, Lei Wu
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Review of application of the I2 and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-03 Dong-Sheng Yang, Xiang-Long Chen, An-Xin Wu
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Vaska's complex–PMHS combination enabled mild and chemoselective reduction of sulfoxides to sulfides with low catalyst loading Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-03 Fang-Fang Xu, Zhong-Lei Ruan, Pei-Qiang Huang
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Enantioselective synthesis of 8-membered lactone derivatives via organocatalytic cascade reactions Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-03 Dong-Sheng Ji, Rui Zhang, Xu-Yan Han, Hai-Long Chai, Yucheng Gu, Xiu-Qin Hu, Peng-Fei Xu
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Cyclization reactions of 1,6-dienes and 1,6-enynes by dual cobalt photocatalysis Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-02 Pei-Ting Li, Zi-Fa Shi, Wei Yu
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Nickel metallaphotoredox-catalyzed C–O bond activation/Csp2–Csp3 coupling enabled by phosphine Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-02 Jiaxi Fang, Ziheng Jian, Huan Liu, Yuting Wang, Xianbo Yu, Zehuai Mou, Huifei Wang
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Iodine-catalyzed intermolecular 1,2-thio (seleno)amination of alkenes with 1,2,3-triazoles and disulfides (diselenides) in air Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-02 Jian Ji, Xuwen Chen, Zongjing Hu, Cong Guan, Jinhua Liu, Yaqi Deng, Shunying Liu
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Spiro-centre substitution effects in the intramolecular spin–spin interactions of spirobiacridine diradicals Org. Chem. Front. (IF 5.4) Pub Date : 2024-04-02 Shinichi Ogawa, Takuya Kanetomo, Masaya Enomoto
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Diazenylation of active methyne compounds via arylazo sulfones Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-23 Ruiqing Wang, Lingkai Kong, Xinyu Zong, Minghui Zhang, Wenyi Chen, Yaxin Liu, Lingjuan Ma, Yulei Zhao
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Neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition to access C–N axially chiral indoles Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-28 Xuan Zhang, Qi Teng, Yanru Ren, Baitong Wei, Chen-Ho Tung, Zhenghu Xu
A Rh-catalyzed neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition of 1,6-diynes and ynamides to generate C–N axially chiral indole derivatives has been developed. The notable features of this method include 100% atom-economy, a wide substrate scope and excellent enantioselectivities by using the easily available chiral SEGPHOS ligands.
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Chiral guanidine catalyzed cyclization reactions of 1,3-enynes for lactone synthesis: switchable H-bond catalysis Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-28 Yongyan Zhang, Lichao Ning, Tianxin Zhu, Zheng Xie, Shunxi Dong, Xiaoming Feng, Xiaohua Liu
H-bonding catalysis has attracted much attention in asymmetric reactions. Taking advantage of guanidine-amides as bifunctional organocatalysts, we successfully achieved cyclization as well as 1,4-conjugate addition/cyclization of azlactones with acyclic and cyclic α-alkynyl-α,β-enones, respectively. The enol-type activation facilitated the generation of lactones via inverse electron-demand hetero-Diels–Alder
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Computational insights into the synergistic interplay of ligand and fluorine effects in palladium-catalyzed regiodivergent decarboxylative allylic alkylation Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-28 Shiyu Wang, Hongli Wu, Xiangyang Tang, Genping Huang
Palladium-catalyzed regiodivergent decarboxylative allylic alkylation of allyl difluoro-β-ketoesters provides a versatile approach for accessing a variety of α,α-difluoroketones. In this report, density functional theory calculations have been performed to investigate the detailed reaction mechanisms and elucidate the origins of regioselectivity. These computations reveal that the reaction is initiated
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A Mn(III)-catalyzed arylboronic acid-based cascade reaction via a nonclassical organometallic-radical mechanism Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-22 Hui-Min Qian, Jian-Dong Zhang, Shun-Jun Ji, Xiao-Ping Xu
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Synthesis of multisubstituted carbazol-4-amines from tetrahydrocarbazol-4-one oximes Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-22 Jiahua Wang, Dandan Gao, Aanuoluwapo O. Oyejobi, Na Ji, Xiang-Ying Tang, Long Wang
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Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-27 Min Tan, Bram B. C. Peters, Pher G. Andersson, Taigang Zhou
The transition metal-catalyzed asymmetric hydrogenation of carbon–carbon double bonds is recognized as one of the most straightforward methods for the preparation of stereopure compounds. Chiral cyclic motifs have widespread applications in organic synthesis and can also be prepared via this strategy. This review summarizes the recent advances (2016–2023) in the stereoselective metal-catalyzed hydrogenation
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Synthesis of 10B-enriched 2,1-borazaronaphthalenes from o-aminostyrenes and 10BF3 Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-26 Weihua Qiu, Jide Zhu, Rencai Tao, Kai Yang, Qiuling Song
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C–H activation-enabled synthesis of a piperazine-embedded azadibenzo[a,g]corannulene analogue Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-21 Lin Huang, Mengyu Qiu, Zhihao Chang, Duncan L. Browne, Jianhui Huang
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DNA-compatible functional group transformations via K2RuO4-mediated oxidation Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-26 Pengyang He, Guixian Zhao, Mengping Zhu, Yangfeng Li, Gong Zhang, Yizhou Li
Functional group transformation represents a potent strategy for enriching the chemical diversity in DNA-encoded chemical library (DEL) synthesis. Within the realm of functional group transformation reactions, oxidation stands out as a predominant and facile approach for delivering altered chemical reactivity. However, reports on DNA-compatible oxidative reactions facilitating functional group transformations
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Palladium-catalyzed [4 + 4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates: access to bridged eight-membered oxygen heterocycles Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-26 Huawei Lin, Biming Mao, Bing Han, Jiayi Luo, Yanqing Ge, Xuerui Zhang, Chang Wang, Hongchao Guo, Chunhao Yuan
In this work, a wide range of bridged eight-membered oxygen heterocycles have been constructed through a novel palladium-catalyzed [4 + 4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates. The reaction demonstrated a broad substrate scope and afforded the products in good yields with excellent stereoselectivities.
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Highly selective separation of toluene/methylcyclohexane based on pagoda[5]arene nonporous adaptive crystals Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-26 Zhongwen Liu, Ming Li, Shuai Fang, Li Shao, Bin Hua, Feihe Huang
Highly selective separation of toluene (Tol) over methylcyclohexane (MCH) has been achieved by utilizing nonporous adaptive crystals of pagoda[5]arene P5. Specifically, P5 demonstrates not only superior binding capability for Tol in solution, but also excellent selectivity for separating Tol from an equivolume Tol/MCH mixture with a high purity of 98.8%.
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Photoredox catalyzed hydroazolylation of alkenes via phosphoranyl radicals Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-26 Fan Zhu, Zhi Qiao, Na He, Chunxiao Nong, Qiping He, Meilan Xi, Xizhong Song, Jun Lin, Jingbo Chen, Yi Jin
Herein, a general protocol for the hydroazolylation of alkenes with N-hydroxyl azoles is reported. These reactions proceed via a phosphoranyl radical that is accessed by photoredox catalysis, followed by radical coupling of the resulting azole radical to the alkene radical. The key point of this reaction lies in the specific binding between the hydroxy group on N-hydroxyazole and alkyl phosphine. This
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DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-26 Shiyu Xu, Zhihui Sun, Pengyutian Liu, Yuanlin Wei, Fan Sun, Man Zhao, Ying Wang, Ming Zhang, Guofeng Li, Hong Liang
A switchable cascade cyclization reaction of ortho-alkynyl arylketones with amines has been developed. The different reaction pathways are controlled by the substituent on the α-carbon of in situ generated ortho-alkynyl arylaldimines. Under the catalysis of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), oxa[3.3.1] bridged ring compounds and 1-naphthylamine derivatives are obtained with high yields and excellent
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Platform for 3-fluoro-3-hydroxyoxindoles: photocatalytic C–N cross-coupling and deaminative oxidation–fluorohydroxylation Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-25 Letian Zhang, Yibin Wang, Jiabin Shen, Hao Xu, Chao Shen
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The synthesis of isoxazolines and dihydrooxazines by Pd-catalyzed oxyalkynylation alkenyl oximes with alkynyl bromides Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-25 Cangzhu Hu, Shiji Xu, Qiang Wang, Jing Sun, Ying Han, Chao-Guo Yan, Lei Wang
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Organocatalyzed double dearomatization reaction of non-functionalized phenols and propargylic alcohols: the important regulating effect of steric hindrance Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-23 Xihong Liu, Boyan Zhu, Panpan Zhou, Jingying Zhang, Anqi Chu, Rui Wang
While Friedel–Crafts (F–C) reaction has been widely used for the preparation of functionalized benzylic compounds, the interrupted F–C reaction that allows for the synthesis of stable dearomatized cyclic systems has rarely been reported. We demonstrate herein that the introduction of an appropriate steric hindrance group around the reactive site of the arene could enable an interrupted F–C reaction
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Tetra-azobenzene extended calix[4]pyrroles: influence of photo-isomerization on chloride binding and its transport through liposomal membranes Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-22 Pedro Ferreira, Gemma Aragay, Pablo Ballester
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An eight-membered ring formed by the Scholl reaction of o-quateraryls Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-19 Xinhe Yang, Man Gao, Han Chen, Qi Gong, Qian Miao
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Contributors to the Organic Chemistry Frontiers Emerging Investigator Series 2022–2023 Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-22
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Solvent dependent hierarchical dual helicity in a fused [4]carbohelicene/quinoline oligoamide foldamer Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-18 Rita Borges-Anastácio, Kevin Moreno, Eric Merlet, Thierry Buffeteau, Brice Kauffmann, Nathan McClenaghan, Yann Ferrand, Céline Olivier
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A Pd(II)-catalyzed denitrative alkyne annulation reaction for the synthesis of cyclopenta[b]chromanes Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-22 Pratiksha Bhorali, Deep J. Kalita, Babulal Das, Sanjib Gogoi
An unprecedented Pd(II)-catalyzed annulation reaction is developed for the synthesis of cyclopenta[b]chromane derivatives bearing a tertiary hydroxyl group. In this reaction, readily available 2-(2-nitrovinyl)phenols are annulated with two molecules of disubstituted alkynes via denitration to afford a wide range of annulated products. Additionally, one novel In(III)-catalyzed dehydroxylative 1,2-phenyl
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Practical photocatalytic hydroalkylation of alkenes with chloroacetates mediated by the formate ion Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-22 Ekaterina V. Malakhova, Vladislav S. Kostromitin, Vitalij V. Levin, Alexander D. Dilman
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Modular synthesis of C2-symmetric nitrogen-containing polyaromatics via visible light-enabled reductive aza-6π electrocyclization Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-22 Qun-Liang Zhang, Qing-Tian Fan, Yirong Zhou, Jingli Zhang, Fang-Lin Zhang
Nitrogen-containing polyaromatic compounds (N-PACs) show wide applications in synthetic chemistry and materials science, but their highly efficient preparation with structurally precise control is a big challenge. Herein, we report an unprecedented one-step modular construction of C2-symmetric N-PACs through visible-light-enabled tandem two-fold direct reduction/aza-6π electrocyclization of nitroarenes
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Access to carbamates and o-aminobenzoates via oxidative carbonylation of amines with CO and alcohols under rhodium/copper catalysis Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-14 Xiaoqi Chen, Xuyao Zhong, Lei Wang, Houyun Teng, Jingsheng Li, Shuai Chen, Rongjing Hu, Lei Yang
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H2O/D2O as the only H/D source for photocatalytic phosphine-mediated radical transfer hydrogenation/deuteration of α-aryl imino esters Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-19 Yao Zhong, Xinhan Li, Xiaohan Zhao, Ruifeng Fan, Jianbin Xu, Baomin Fan
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Photoinduced cobalt catalyzed site selective alkylation of 2-pyridones Org. Chem. Front. (IF 5.4) Pub Date : 2024-03-19 Chenyue Li, Jing Li, Zibin Jiang, Yiwei Xu, Hujie Xiong, Fei-Long Liu, Tingting Liu, Fei Ye, Chenggui Wu
Herein, a selective C3- and C6-alkylation reaction of 2-pyridone by a direct C–H functionalization approach was used to access 2-pyridone derivatives. Under photocatalytic reaction conditions, alkyl halides or methanesulfonates were used as alkyl radical sources utilizing cobalt catalyzed reductive cleavage. The formation of carbon–carbon bonds exhibited site-selectivity at either the C3 or C6 position