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DNA-compatible functional group transformations via K2RuO4-mediated oxidation

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00203B, Research Article
Pengyang He, Guixian Zhao, Mengping Zhu, Yangfeng Li, Gong Zhang, Yizhou Li
K2RuO4-mediated oxidation offers a DNA-compatible method for functional group transformations, enabling alcohol-to-carboxylic acid and amine-to-nitrile conversions valuable for DNA-encoded library synthesis.
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Neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition to access C–N axially chiral indoles

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00042K, Research Article
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.
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Computational insights into the synergistic interplay of ligand and fluorine effects in palladium-catalyzed regiodivergent decarboxylative allylic alkylation

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00147H, Research Article
Shiyu Wang, Hongli Wu, Xiangyang Tang, Genping Huang
DFT calculations were performed to investigate palladium-catalyzed decarboxylative allylic alkylation of allyl difluoro-β-ketoesters. The synergistic effects of ligand and fluorine substituents on regioselectivity were uncovered.
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Chiral guanidine catalyzed cyclization reactions of 1,3-enynes for lactone synthesis: switchable H-bond catalysis

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00374H, Research Article
Yongyan Zhang, Lichao Ning, Tianxin Zhu, Zheng Xie, Shunxi Dong, Xiaoming Feng, Xiaohua Liu
Cyclization and 1,4-conjugate addition/cyclization between 2-activated 1,3-enynes and azlactones were achieved with chiral guanidine-amides for enol-type activation to yield a range of δ-lactone derivatives.
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Synthesis of a helical boron-doped PAH by post-functionalization of 3,9-diboraperylene

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00421C, Research Article
Carina Mützel, Kazutaka Shoyama, Ana-Maria Krause, Frank Würthner
A doubly helical boron-doped polycyclic aromatic hydrocarbon was synthesized, which showed a low LUMO level, a high absorption coefficient and fluorescence (ΦF = 0.73), combined with a one-dimensional π–π stacking interaction in the solid state.
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Enantioselective synthesis of 8-membered lactone derivatives via organocatalytic cascade reactions

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00148F, Research Article
Dong-Sheng Ji, Rui Zhang, Xu-Yan Han, Hai-Long Chai, Yucheng Gu, Xiu-Qin Hu, Peng-Fei Xu
The challenging 8-membered lactone derivatives bearing two vicinal chiral stereocenters were synthesized via a cascade reaction mediated by the chiral squaramide.
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Review of application of the I2 and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00396A, Review Article
Dong-Sheng Yang, Xiang-Long Chen, An-Xin Wu
The synthesis of small molecules and complex scaffolds is one of the most important topics in organic synthesis.
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Asymmetric [3 + 2] cycloaddition of donor–acceptor cyclopropanes with azadienes enabled by Brønsted base catalysis

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00002A, Research Article
Shu Li, Zhi-Hong Dong, Si-Yu Dan, Mei-Jun Zheng, Teng Long, Jie Zhan, Qing Zhou, Wen-Dao Chu, Quan-Zhong Liu
A chiral bifunctional Brønsted base-catalyzed enantioselective [3 + 2] cycloaddition of D–A cyclopropanes and azadienes is reported. The protocol features broad substrate scope, mild reaction conditions and high functional group tolerance.
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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

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00141A, Research Article
Tong Xiong, Yi-Zhao Xu, Yao Wang, You-Cai Xiao, Fen-Er Chen
An asymmetric organocatalytic formal [4 + 2] cycloaddition/annulation cascade of ortho-quinone methides with 2-isocyanatomalonate diesters has been reported.
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Decarbonylative C(sp2)–C(sp2) reductive cross-coupling of aroyl fluorides with aryl bromides by palladium/cobalt co-catalysis

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00305E, Research Article
Chen He, Zhiyong Song, Wei Yao, Rui Lin, Yuanhong Ma
Herein, we report a decarbonylative C(sp2)–C(sp2) reductive cross-coupling of aroyl fluorides with aryl bromides by palladium and cobalt co-catalysis.
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Electrochemically dehydrogenative C(sp2)–H/S–H cross-coupling: efficient synthesis of ortho-aminophenyl thioglycoside derivatives

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00171K, Research Article
Li-Yan Hu, Li Zhu, Shen-Yuan Zhang, Yu-Xin Guo, Yuan Li, Jie Zhu, Lei Wu
A method has been reported for synthesizing aryl thioglycosides through direct electrocatalytic dehydrogenative C(sp2)–H/S–H cross-coupling.
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Nickel metallaphotoredox-catalyzed C–O bond activation/Csp2–Csp3 coupling enabled by phosphine

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00310A, Research Article
Jiaxi Fang, Ziheng Jian, Huan Liu, Yuting Wang, Xianbo Yu, Zehuai Mou, Huifei Wang
A novel and general nickel/photoredox dual catalysis platform for benzyl alcohol C–O bond activation/Csp2–Csp3 cross coupling of benzothiazolyl bromide and free alcohol, enabled by the catalytic generation of an alkyl radical, is reported.
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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

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO90034K, Correction
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Zhong-Yi Mao, Hui Geng, Tian-Tian Zhang, Yuan-Ping Ruan, Jian-Liang Ye, Pei-Qiang Huang
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Visible-light-mediated catalyst-free synthesis of trifluoromethyl(spiro)-epoxides bearing contiguous quaternary centers

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00184B, Research Article
Jingchuan Lin, Yu Zhang, Jinxin Wang, Xinyu Han, Shenglan Zhu, Tong Li, Yanping Zhu, Wei-Dong Zhang
Herein, we describe a non-covalent complex-mediated epoxidation strategy that can yield highly selective central spiro-epoxides by irradiation with visible light without the need for catalyst addition.
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Base-induced azofluoroalkylation of unactivated alkenes via halogen atom transfer

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Org. Chem. Front., 2024, 11,2161-2170
DOI: 10.1039/D3QO02114A, Research Article
Jing Zhang, Yanchuang Zhao, Yu-Yi Zhu, Peng Lei, Hanru Liu, Chang-Sheng Wang, Shuya Xing, Yong Liu, Shao-Fei Ni, Thomas Castanheiro, Li-Wen Xu, Xinxin Shao
A base-induced three-components coupling employing unactivated alkenes, fluoroalkyl iodides and diazonium salts under mild reaction conditions has been developed.
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A formal (3 + 2) annulation–Cannizzaro cascade of bifunctional peroxides for the synthesis of dihydrofurans

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Org. Chem. Front., 2024, 11,2215-2219
DOI: 10.1039/D4QO00215F, Research Article
Yiwei Chen, Min Gao, Qianlan Xu, Jiumeng Zhang, Lin Hu
Tunable tandem processes of bifunctional peroxides allow the divergent construction of functionalized dihydrofurans and epoxides by simply changing the basic conditions.
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Iridium-catalyzed reductive γ-lactonization of ortho-acylbenzoic acids in water: sustainable access to phthalides

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Org. Chem. Front., 2024, 11,2220-2230
DOI: 10.1039/D3QO02019C, Research Article
Yang Chen, Jingyu Zhang, Hongguang Du, Renshi Luo, Jiaxi Xu, Zhanhui Yang
Iridium-catalyzed reductive γ-lactonization of ortho-acylbenzoic acids in water provides a practical and sustainable route to phthalides.
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Electrode-switchable: exploring this new strategy to achieve regiodivergent azidoiodination of alkenes

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Org. Chem. Front., 2024, 11,2189-2194
DOI: 10.1039/D3QO01935G, Research Article
Xin-Lei Sun, Chen-Xi Xia, Yue Ren, Yu-Jin Li, Zhi-Qian Cao, Ling-Guo Meng
An “electrode-switchable” organic electrochemistry method for the azidoiodination of alkenes, where the choice of anode dictates the regiodivergent alkene azidoiodination, reveals a novel pathway for controlled regioisomers.
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Photo-induced catalyst-free formal carbon insertion of acylsilanes into B–B and B–Si bonds

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Org. Chem. Front., 2024, 11,2339-2343
DOI: 10.1039/D4QO00139G, Research Article
Xiongxiong Lu, Qingbin Zhao, Hao Zhang, Pan Xu, Xuenian Chen, Zhenxing Liu
A formal carbon insertion of acylsilanes into B–B and B–Si bonds has been developed. The in situ formed siloxycarbene under blue LED irradiation worked as the intermediate for the reaction. When 2-furyl and 2-thiophenyl acylsilanes were used, the B(pin) ring was enlarged to a six-membered ring.
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Origin of site-selectivity of hydrogen atom transfer in carbohydrate C–H alkylations via photoredox catalysis

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Org. Chem. Front., 2024, 11,2269-2276
DOI: 10.1039/D4QO00073K, Research Article
Yujie Ji, Lingfei Hu, Han Gao, Yan-Bo Wu, Xiangying Lv, Gang Lu
Two major factors, i.e., C–H σ orbital energy and C–H BDE, account for the HAT site-selectivity of carbohydrates with the quinuclidine radical cation.
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Electron donor–acceptor complex photoactivation for deaminative alkynylation, alkenylation and allenylation: a comprehensive study

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Org. Chem. Front., 2024, 11,2231-2240
DOI: 10.1039/D4QO00177J, Research Article
Romain Lapierre, Lina Truong, Matthieu Hedouin, Hassan Oulyadi, Bruno Schiavi, Alexandre Jean, Philippe Jubault, Thomas Poisson
Herein, we disclose our study toward photoinduced deaminative alkynylation, alkenylation and allenylation.
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A dearomatization–rearomatization strategy for construction of 4H-quinolizin-4-ones via C–H bond functionalization of pyridines

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Org. Chem. Front., 2024, 11,2319-2325
DOI: 10.1039/D3QO01990J, Research Article
Dong Qiu, Yijin Su
Herein, the synthesis of 4H-quinolizin-4-ones from N-(2-methoxy-2-oxoethyl) pyridinium salts and alkenes through dearomative cycloaddition and rearomative ring expansion has been developed.
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Nickel/photoredox-catalyzed carbonylative transformations of α-phosphorus-, α-sulfur-, and α-boron-substituted alkyl halides

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Org. Chem. Front., 2024, 11,2297-2305
DOI: 10.1039/D4QO00167B, Research Article
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Le-Cheng Wang, Xiao-Feng Wu
A novel dual nickel/photoredox catalyzed direct amino- and alkoxycarbonylation of α-heteroatom substituted organohalides has been developed.
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Palladium-catalyzed asymmetric [4 + 3] cycloaddition of acyclic α,β-unsaturated imines with trimethylenemethane donors: access to chiral non-fused azepines

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Org. Chem. Front., 2024, 11,2326-2331
DOI: 10.1039/D4QO00064A, Research Article
Ting-Peng Li, Shuixiu Su, Jia-Huan Shen, Meng Zang, Yang-Zi Liu, Quannan Wang, Wei-Ping Deng
An efficient approach for the construction of non-fused azepines in good yields with high enantioselectivity via Pd-catalyzed asymmetric [4 + 3] cycloaddition was developed.
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Contributors to the Organic Chemistry Frontiers Emerging Investigator Series 2022–2023

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Org. Chem. Front., 2024, 11,2149-2154
DOI: 10.1039/D4QO90025A, Profile

This profile article showcases researchers who have contributed an article to the Organic Chemistry Frontiers Emerging Investigator Series.
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Correction: Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids

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Org. Chem. Front., 2024, 11,2418-2418
DOI: 10.1039/D4QO90029D, Correction
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Junjie Ying, Jingrong Huang, Chenguang Liu, Fa-Jie Chen, Chunfa Xu, Fen-Er Chen
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NHC and photoredox catalysis dual-catalyzed 1,4-mono-/di-fluoromethylative acylation of 1,3-enynes

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00372A, Research Article
Jiuli Xia, Ruiyang Ma, Lihong Wang, Jiaqiong Sun, Guangfan Zheng, Qian Zhang
NHC and photocatalysis dual-catalyzed mono/difluoromethylative acylation of 1,3-enynes was realized, providing fluormethyl-substituted allenyl ketones. SO2 might play a critical role in achieving high reactivity and selectivity.
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Assembly of ionic supramolecular polymers using a decacationic pillar[5]arene to noncovalently crosslink hyaluronic acid for short DNA delivery

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00447G, Research Article
Qian Li, Danying Ma, Yue-Yang Liu, Hui Wang, Wei Zhou, Dan-Wei Zhang, Zhan-Ting Li
A multicationic pillar[5]arene noncovalently crosslinks hyaluronic acid to afford ionic supramolecular polymers for intramolecular delivery of short DNA.
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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

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00351A, Research Article
Fei Liu, Fengqing Wang, Qin Li, Bingbing Dai, Weiguang Sun, Jianguo Li, Chunmei Chen, Yonghui Zhang, Hucheng Zhu
Lovastatin derivatives aculeatones A–F (1–6) with lipid-lowering activity were isolated from Aspergillus aculeatus. 1 and 2 represent the first examples with a 6/6/3-tricyclic scaffold and the biomimetic formation of 1 was achieved starting from 3.
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NBN/BNB-doped phenalenyl homo- and heterodyads: structural uniformity but optoelectronic diversity

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00468J, Research Article
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Alexander S. Scholz, Thomas Froitzheim, Michael Bolte, Hans-Wolfram Lerner, Jan-M. Mewes, Matthias Wagner
Phenylene-bridged homo- and heterodyads of NBN- and BNB-phenalenyls were synthesized. The heterodyads show ambipolar redox character and aggregation-induced emission in the solid state.
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Copper-catalyzed oxidative sulfenylation and alkylation of indolin-2-ones for direct construction of sulfur-substituted quaternary carbons

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00491D, Research Article
Yun-Hao Zhang, Yi-Nuo Wang, Zi-Yu Liu, Si-Han Zheng, Guang-Lin Li, Dexin Feng, Da-Zhen Xu
A rapid and green one-pot access to S-substituted quaternary carbon centers from commercially available feedstock chemicals has been established, providing complex molecules with high chemoselectivity by the use of air as the terminal oxidant.
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A retro-Mannich mediated transformation of Morita–Baylis–Hillman ketones to saturated imidazo[1,2-a]pyridines

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00352G, Research Article
Sachin Sharma, Ajit Kumar Jha, Srinivasan Easwar
Two fruits felled with one stone! – a proof of mechanism and a synthetic method that delivers a privileged heterocyclic motif.
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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

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00371C, Research Article
Yao Yao, Yuan Yu, Ming-Liang Shi, Xin-Yue Fan, Ru-De Lin, Kun Li, Wen-Dian Li, Fei-Yan Tao, Na Wang
The effective combination of photocatalysis and enzyme catalysis has been widely utilized for the synthesis of high-value-added products.
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Fully atom-economic access to spiro-cyclic skeletons through photoredox-induced hydrogen transfer/Giese addition/dearomative cyclization/protonation cascade

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00317A, Research Article
Guohui Zeng, Hui Luo, Kai Jiang, Jianpeng Cai, Biaolin Yin
Amine-tethered spiro-cyclic skeletons were obtained through photo-induced 100%-atom-economic dearomatization, involving the cleavage of the α-C(sp3)–H of amines. Pentacyclic framework was achieved from pyridinyl ring within two steps.
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Catalytic Ortho C-H Methylation and Trideuteromethylation of Arylthianthrenium Salts via the Catellani Strategy

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO00506F, Research Article
Chen Chen, Xiao-Xu Zhang, Zi-Yi Wang, Chunjie Ni, Bolin Zhu
We reported a Pd/NBE cooperative catalyzed ortho C−H methylation and trideuteromethylation of arylthianthrenium salts, enabling the efficient synthesis of a wide variety of (trideutero)methylated arenes in moderate to good yields....
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Halogen-Bond-Promoted Direct Cross-Coupling of Ethyl 3-bromo-3-alkyl-2,2-difluoropropanoate with Coumarins/Quinolinones

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Org. Chem. Front., 2024, Accepted Manuscript
DOI: 10.1039/D4QO00484A, Research Article
Guoliang Pu, Shi-Yuan Song, Jian Yang, Peng Guo, Jia Jia, Peijun Liu, Xuefei Li, Ping Liu, Chun-Yang He
Herein, we developed a practical method for the direct cross-coupling of ethyl 3-bromo-3-alkyl-2,2-difluoropropanoate with coumarins/quinolinones, leveraging a halogen bond as the pivotal non-covalent interaction. Employing this protocol, a library of...
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Expedient deaminative phosphorylation and sulfonylation of benzylic tertiary amines enabled by difluorocarbene

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00412D, Research Article
Chengbo Li, Yu Guo, Jianke Su, Xinyuan Hu, Qingqing Xuan, Qiuling Song
A deaminative functionalization of aliphatic tertiary amines via the cleavage of C(sp3)–N bonds under transition metal-free conditions was disclosed, which goes through SN2 reaction with various phosphorus and sulfur nucleophiles.
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Thiourea as a precatalyst for the electron donor–acceptor complex photoactivation platform of oxime esters

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Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO00424H, Research Article
Haichen Mao, Yuting Zhang, Hengrong Cao, Qianqian Shi, Yu Lan, Junbiao Chang, Bo Zhu
A novel electron donor–acceptor (EDA) complex catalysis strategy has been developed using thiourea as a precatalyst under blue LED irradiation. Using 2–5 mol% of thiourea, various nitrogen-containing compounds were successfully synthesized.
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Integrating continuous flow reaction and work-up: chiral amine resolution, separation and purification using a novel coalescing filter system

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React. Chem. Eng., 2024, Accepted Manuscript
DOI: 10.1039/D4RE00442F, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Bethan May Rowley, Lisa Alice Thompson, Luke Power, James Daglish, Emma Parks, James Birbeck, Stephen P Marsden, Nikil Kapur, John Blacker
To maximize the benefits of a continuous flow reaction, a continuous work-up is also needed. Herein, we present a process design and novel equipment for a continuous amine resolution reaction,...
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A self-adsorption molecule passivated interface enables efficient and stable lithium metal batteries

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Energy Environ. Sci., 2024, Advance Article
DOI: 10.1039/D4EE02903H, Paper
Gongxun Lu, Xinru Wu, Miaofei Huang, Mengtian Zhang, Zhihong Piao, Xiongwei Zhong, Chuang Li, Yanze Song, Chengshuai Chang, Kuang Yu, Guangmin Zhou
Self-adsorbing molecules stabilize electrode interfaces and inhibit solvent decomposition to ensure high-voltage stability of lithium metal batteries.
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Efficient Fully Textured Perovskite Silicon Tandems with Thermally Evaporated Hole Transporting Materials

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Energy Environ. Sci., 2024, Accepted Manuscript
DOI: 10.1039/D4EE03899A, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Bhushan Kore, Oussama Er-raji, Oliver Fischer, Adrian Callies, Oliver Schultz-Wittmann, Patricia Samia Cerian Schulze, Martin Bivour, Stefaan De Wolf, Stefan W Glunz, Juliane Borchert
Fully textured perovskite silicon tandem solar cells effectively minimize the reflection losses and are compatible with industrial silicon production lines. To facilitate scalability and industrial deployment of perovskite silicon tandems...
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Contribution of an instructional module incorporating PhET simulations to Rwandan students' knowledge of chemical reactions, acids, and bases through social interactions

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Chem. Educ. Res. Pract., 2024, Advance Article
DOI: 10.1039/D4RP00105B, Paper
Jean-Baptiste Ndagijimana, Jeannette Musengimana, Henriette Mushimiyimana, Evode Mukama, Olivier Habimana, Paulin Manirakiza, Jean Claude Dushimimana, Jean Pierre Alpha Munyaruhengeri, Samia Khan, Elizabeth Lakin
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