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Rhodium-catalyzed asymmetric transfer hydrogenation of 4-quinolone derivatives

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Org. Chem. Front., 2020, 7,975-979
DOI: 10.1039/C9QO01514K, Research Article
Bin He, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
4-Quinolone derivatives were conveniently reduced to 1,2,3,4-tetrahydroquinoline-4-ols with excellent enantioselectivities through asymmetric transfer hydrogenation using a tethered rhodium complex and formic acid/triethylamine as the hydride source.
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Expeditious access of chromone analogues via a Michael addition-driven multicomponent reaction

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Org. Chem. Front., 2020, 7,987-992
DOI: 10.1039/D0QO00145G, Research Article
Jie Lei, Yong Li, Liu-Jun He, Ya-Fei Luo, Dian-Yong Tang, Wei Yan, Hui-Kuan Lin, Hong-yu Li, Zhong-Zhu Chen, Zhi-Gang Xu
A Michael addition-driven four-component reaction (4-CR) with four Ugi inputs was developed and utilized for the synthesis of chromone derivatives and tetrazole substituted chromones under mild reaction conditions.
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HKOCl-4: a rhodol-based yellow fluorescent probe for the detection of hypochlorous acid in living cells and tissues

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Org. Chem. Front., 2020, 7,993-996
DOI: 10.1039/D0QO00081G, Research Article
Xiaoyu Bai, Bowei Yang, Hansen Chen, Jiangang Shen, Dan Yang
Highly sensitive and selective yellow probes, HKOCl-4 and its derivatives, have been developed for detecting endogenous HOCl in cytosol and mitochondria of living cells. In addition, visualization of HOCl production in ischemic stroke model has been achieved with HKOCl-4r.
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Copper-catalyzed tandem phosphorylative allenylation/cyclization of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species: access to C2-phosphorylmethylindoles

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Org. Chem. Front., 2020, 7,980-986
DOI: 10.1039/D0QO00159G, Research Article
Xiao-Yan Liu, Yun-Xiang Zou, Hai-Liang Ni, Jing Zhang, Hong-Bo Dong, Long Chen
A novel method to synthesize C2-phosphorylmethylindoles via the carbocation formation initiated tandem phosphorylative allenylation/cyclization of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species has been developed.
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Oxidative N-heterocyclic carbene-catalyzed [3 + 3] annulation reaction of enals with benzofuran-3-ones: efficient access to benzofuran-fused δ-lactones

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Org. Chem. Front., 2020, 7,1011-1015
DOI: 10.1039/D0QO00161A, Research Article
Zhan-Yong Wang, Ting Yang, Kai-Kai Wang, Rongxiang Chen, Menghan Liu, Hongxin Liu
A facile route to benzofuran-fused δ-lactones was developed via an N-heterocyclic carbene-catalyzed [3 + 3] annulation reaction, giving the expected products in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee).
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The key role of protodeauration in the gold-catalyzed reaction of 1,3-diynes with pyrrole and indole to form complex heterocycles

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Org. Chem. Front., 2020, 7,997-1005
DOI: 10.1039/C9QO01544B, Research Article
Ioannis Stylianakis, Olalla Nieto Faza, Carlos Silva López, Antonios Kolocouris
The mechanism of indole and carbazole formation via a formal [4 + 2] cycloaddition strategy is dominated by the protodeauration step.
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Construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation utilizing a ferrocene derived bifunctional phosphine catalyst

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Org. Chem. Front., 2020, 7,1016-1021
DOI: 10.1039/D0QO00140F, Research Article
Wenjun Luo, Bingxuan Shao, Jingyi Li, Xiao Xiao, Dingguo Song, Fei Ling, Weihui Zhong
Regional and stereoselective construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation catalyzed by ferrocene derived bifunctional phosphine.
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Palladium-catalyzed double carbonylation of propargyl amines and aryl halides to access 1-aroyl-3-aryl-1,5-dihydro-2H-pyrrol-2-ones

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Org. Chem. Front., 2020, 7,1006-1010
DOI: 10.1039/D0QO00007H, Research Article
Jun Ying, Zhengjie Le, Zhi-Peng Bao, Xiao-Feng Wu
A palladium-catalyzed carbonylative procedure for the synthesis of 1-aroyl-3-aryl-1,5-dihydro-2H-pyrrol-2-ones from propargyl amines and aryl halides with TFBen as the CO source has been developed.
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Total synthesis of tumor-associated KH-1 antigen core nonasaccharide via photo-induced glycosylation

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00314J, Research Article
Bo-Han Li, Wenlong Yao, Hong Yang, Congying Wu, De-Cai Xiong, Yuxin Yin, Xin-Shan Ye
KH-1 antigen core nonasaccharide was efficiently assembled by photo-induced glycosylation.
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Double allylic defluorinative alkylation of 1,1-bisnucleophiles with (trifluoromethyl)alkenes: construction of all-carbon quaternary centers

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00121J, Research Article
Yingying Cai, Hao Zeng, Chuanle Zhu, Chi Liu, Guangying Liu, Huanfeng Jiang
Synthesis of symmetric gem-difluoroalkene substituted products bearing all-carbon quaternary centers via double allylic defluorinative alkylation of 1,1-bisnucleophiles with (trifluoromethyl)alkenes.
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Folding of fluorinated oligoarylenes into non-alternant PAHs with various topological shapes

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00370K, Research Article
Vladimir Akhmetov, Andreas Förtsch, Mikhail Feofanov, Sergey Troyanov, Konstantin Amsharov
An unprecedented [6]helicene's cavity closure indicating the possibility of introducing seven-membered rings via alumina-mediated C–F activation is shown.
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Rh-Catalyzed nitrene alkyne metathesis/formal C–N bond insertion cascade: synthesis of 3-iminoindolines

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00294A, Research Article
Kemiao Hong, Su Zhou, Wenhao Hu, Xinfang Xu
A Rh-catalyzed nitrene/alkyne metathesis (NAM) cascade reaction terminated by a formal C–N bond insertion has been developed, which provides facile access to the tricyclic 3-iminoindolines in good yields with broad substrate scope.
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Access to SCN-containing thiazolines via electrochemical regioselective thiocyanothiocyclization of N-allylthioamides

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00300J, Research Article
Yan-An Zhang, Zhong Ding, Peng Liu, Wei-Si Guo, Li-Rong Wen, Ming Li
An electrochemical thiocyclization of N-allylthioamides has been developed for the synthesis of SCN-containing 2-thiazolines and NCS-containing thiazines.
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Pyridine tetrafluoro-λ6-sulfanyl chlorides: spontaneous addition to alkynes and alkenes in the presence or absence of photo-irradiation

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00339E, Research Article
Kiyoteru Niina, Kazuhiro Tanagawa, Yuji Sumii, Norimichi Saito, Norio Shibata
A radical addition reaction of Py-SF4Cl to alkynes and alkenes provide pyridine-SF4-alkenes and pyridine-SF4-alkanes under blue LED light irradiation or absence of light irradiation in CPME or without solvent.
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Discovery of new polycyclic polyprenylated acylphloroglucinols with diverse architectures as potent cyclooxygenase-2 inhibitors

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00259C, Research Article
Shuangshuang Xie, Changxing Qi, Yulin Duan, Qianqian Xu, Yaping Liu, Yingying Huang, Xu Yin, Weiguang Sun, Yuan Zhou, Yonghui Zhang
Cyclooxygenase-2 (COX-2) is a significant therapeutic target of chronic inflammatory diseases.
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Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00348D, Research Article
Luyao Li, Bo Zhu, Huihui Fan, Zhiyong Jiang, Junbiao Chang
Herein, we report a chiral bifunctional thiourea catalyzed asymmetric Michael addition reaction between 2-(trifluoromethyl)oxazol-5(2H)-one as a direct C-2-position nucleophile to 4-nitro-5-styrylisoxazoles for the first time.
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Visible-light mediated oxidative ring expansion of anellated cyclopropanes to fused endoperoxides with antimalarial activity

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00168F, Research Article
Simon Budde, Felix Goerdeler, Johannes Floß, Peter Kreitmeier, Elliot F. Hicks, Oren Moscovitz, Peter H. Seeberger, Huw M. L. Davies, Oliver Reiser
Hetero- and carbocyclic anellated cyclopropanes were converted in one step by a visible light induced photooxidation to their corresponding polycyclic endoperoxides, which show promising antimalarial activity.
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Transition metal-catalyzed coupling of heterocyclic alkenes via C-H activation: Recent trends and applications

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Org. Chem. Front., 2020, Accepted Manuscript
DOI: 10.1039/D0QO00279H, Review Article
Sundaravel Vivek Kumar, Sonbidya Banerjee, Tharmalingam Punniyamurthy
Heterocyclic alkenes represent an important class of reactive feedstock and valuable synthons for the synthesis of biologically important heterocyclic scaffolds. Although functionalized heterocyclic alkenes and their derivatives can be accessed...
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Access to cyano-substituted pyrazolines through copper-catalyzed cascade cyanation/cyclization of unactivated olefins

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00282H, Research Article
Fei Meng, Qin Fang, Weidong Yuan, Ning Xu, Shujun Cao, Jianlin Chun, Jie Li, Honglin Zhang, Yingguang Zhu
A mild copper-catalyzed cascade cyanation/cyclization of hydrazone-tethered unactivated olefins was developed for the efficient and practical synthesis of cyano-containing pyrazolines.
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Organocatalytic 1,5-trifluoromethylthio-sulfonylation of vinylcyclopropane mediated by visible light in the water phase

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00343C, Research Article
Junkai Liu, Hong Yao, Xinnan Li, Hongyu Wu, Aijun Lin, Hequan Yao, Jinyi Xu, Shengtao Xu
1,2-Difunctionalization has developed into a robust tool for the preparation of complex organic molecules, and remote difunctionalization has also aroused widespread interest to achieve pluripotency of difunctionalization.
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Preparation of a mechanically interlocked polymer from a linear supramolecular polymer

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00315H, Research Article
Zibin Zhang, Kechang Sun, Leqiong Jin, Chunsong Xie, Shijun Li
We transformed a linear supramolecular polymer into a mechanically interlocked polymer by photoisomerization.
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Ag2O-catalysed nucleophilic isocyanation: selective formation of less-stable benzylic isonitriles

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00336K, Research Article
Taiga Yurino, Yuji Tange, Ryutaro Tani, Takeshi Ohkuma
Both primary and secondary benzylic isonitriles were exclusively produced by the Ag2O-catalysed reaction of benzylic phosphates and trimethylsilyl cyanide without formation of the thermodynamically favoured regioisomers, benzylic nitriles.
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Discrete boronate ester ladders from the dynamic covalent self-assembly of oligo(phenylene ethynylene) derivatives and phenylenebis(boronic acid)

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Org. Chem. Front., 2020, 7,1082-1094
DOI: 10.1039/D0QO00083C, Research Article
Vasileios Drogkaris, Brian H. Northrop
Reversible boronate ester chemistry enables the controlled, dynamic self-assembly of olig(phenylene ethynylene)s into highly conjugated ladder frameworks.
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Differential formation of nitrogen-centered radicals leading to unprecedented, regioselective bromination of N,N'-(1,2-phenylene)bisamides and 2-amidophenols

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Org. Chem. Front., 2020, 7,1095-1106
DOI: 10.1039/C9QO01508F, Research Article
Damoder Reddy Motati, Dilipkumar Uredi, Amarender Goud Burra, J. Phillip Bowen, Frank R. Fronczek, Clint R. Smith, E. Blake Watkins
A highly efficient, site-selective, visible light-accelerated, remote C–H halogenation of unsymmetrical aromatic bisamides/amidoesters has been developed.
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Topomeric aza/thia cryptands: synthesis and theoretical aspects of in/out isomerism using n-alkyl bridging

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Org. Chem. Front., 2020, 7,1164-1176
DOI: 10.1039/D0QO00123F, Research Article
Ian S. Taschner, Tia L. Walker, Sharath Chandra M., Briana R. Schrage, Christopher J. Ziegler, Xinfeng Gao, Steven E. Wheeler
A series of heterobicyclic aza/thia-lactams and cryptands incorporating changes in n-alkyl bridging length have been synthesized, characterized, chelated to heavy metals and computationally assessed.
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Synthesis and biological evaluation of suffrutines A, B and their N-fused analogues

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Org. Chem. Front., 2020, 7,1122-1131
DOI: 10.1039/D0QO00050G, Research Article
Zefeng Zhu, Chun Chen, Jingxing Jiang, Qianzhong Zhang, Zhibo Du, Shuxian Wei, Xianheng Song, Jie Tang, Jinping Lei, Zhuofeng Ke, Yong Zou
The synthesis, structure confirmation, stability and isomerization features of suffrutines A, B and their N-fused analogues were reported. Biological tests showed that the introduction of nitrogen atom might be beneficial to the anticancer activity.
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Insights into N-heterocyclic carbene and Lewis acid cooperatively catalyzed oxidative [3 + 3] annulation reactions of α,β-unsaturated aldehyde with 1,3-dicarbonyl compounds

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Org. Chem. Front., 2020, 7,1113-1121
DOI: 10.1039/D0QO00091D, Research Article
Xinghua Wang, Yang Wang, Jinshuai Song, Donghui Wei
N-Heterocyclic carbene and Lewis acid cooperatively catalyzed oxidative [3 + 3] annulation reactions of 1,3-dicarbonyl compounds have been systematically studied in theory.
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Access to branched allylsilanes by nickel-catalyzed regioselective hydrosilylation of allenes

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Org. Chem. Front., 2020, 7,1132-1136
DOI: 10.1039/D0QO00156B, Research Article
Jia-Hao Zeng, Jun-Jia Chen, Li Chen, Zhuang-Ping Zhan
A Ni(acac)2/Xantphos-catalyzed hydrosilylation of allenes has been developed.
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Toward C2-nitrogenated chromones by copper-catalyzed β-C(sp2)–H N-heteroarylation of enaminones

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Org. Chem. Front., 2020, 7,1107-1112
DOI: 10.1039/D0QO00065E, Research Article
Tian Luo, Jie-Ping Wan, Yunyun Liu
The synthesis of C2-nitrogenated chromones has been performed via reactions of enaminones and nitrogen nucleophiles based on an unconventional β-C–H bond functionalization and a featured chromone annulation of enaminones.
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Direct synthesis of annulated indoles through palladium-catalyzed double alkylations

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Org. Chem. Front., 2020, 7,1149-1157
DOI: 10.1039/D0QO00135J, Research Article
Yadong Gao, Jianhua Li, Songlin Bai, Daoquan Tu, Chao Yang, Zhiwen Ye, Bingcheng Hu, Xiangbing Qi, Chao Jiang
A facile, one-step synthesis of annulated indoles from (N–H) indoles and dibromoalkanes was developed through a palladium-catalyzed double alkylation process.
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The origin of regioselectivity in Cu-catalyzed hydrocarbonylative coupling of alkynes with alkyl halides

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Org. Chem. Front., 2020, 7,1137-1148
DOI: 10.1039/D0QO00214C, Research Article
Shengnan Liu, Jianbiao Liu, Qiong Wang, Jin Wang, Fang Huang, Wenjuan Wang, Chuanzhi Sun, Dezhan Chen
Steric interactions mediate a switch between a ketone and allylic alcohol in Cu-catalyzed hydrocarbonylative coupling of alkynes with alkyl halides.
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Rh(III)-Catalyzed switchable C–H functionalization of 2-(1H-pyrazol-1-yl)pyridine with internal alkynes

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Org. Chem. Front., 2020, 7,1158-1163
DOI: 10.1039/D0QO00248H, Research Article
Shaonan Wu, Zhuo Wang, Dianxue Ma, Chen Chen, Bolin Zhu
We reported a Rh(III)-catalyzed switchable C–H functionalization of 2-(1H-pyrazol-1-yl)pyridine with internal alkynes, which provided diversiform functionalized N,N-bidentate chelating compounds.
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Anthranils: versatile building blocks in the construction of C–N bonds and N-heterocycles

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Org. Chem. Front., 2020, 7,1177-1196
DOI: 10.1039/D0QO00163E, Review Article
Yang Gao, Jianhong Nie, Yanping Huo, Xiao-Qiang Hu
This review article provides an overview of the recent progress in the transformations of anthranils, which have emerged as versatile building blocks in the assembly of various C–N bonds and medicinally active heterocyclic systems.
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An Aspidosperma-type alkaloid dimer from Tabernaemontana bovina as a candidate for the inhibition of microglial activation

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00296H, Research Article
Yang Yu, Si-Meng Zhao, Mei-Fen Bao, Xiang-Hai Cai
As a representative of twelve undescribed Aspidosperma-type alkaloid dimers, tabernaemontine F (6) inhibited microglial activation by blocking P38 MAPK activation, revealing a potential candidate for chronic neurodegenerative diseases.
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Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00448K, Research Article
Jun Kikuchi, Yuki Aizawa, Masahiro Terada
An enantioselective intermolecular addition reaction of 1,1,2-trisubstituted and 1,2- disubstituted simple olefins with ethyl glyoxylate was developed using F10BINOL-derived N-sulfonyl phosphoramide as a chiral strong Brønsted acid catalyst.
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An exocyclic π-system extension of the phenanthriporphyrin framework: towards azaaceneporphyrinoids

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Org. Chem. Front., 2020, Advance Article
DOI: 10.1039/D0QO00436G, Research Article
Bartosz Szyszko, Damian Dróżdż, Aleksandra Sarwa, Sebastian G. Mucha, Agata Białońska, Michał J. Białek, Katarzyna Matczyszyn, Lechosław Latos-Grażyński
An exocyclic π-extension of phenanthriporphyrin reduces the macrocyclic antiaromaticity of the formed expanded carbaporphyrinoids.
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Phosphine/Palladium Cooperative Catalysis: Enantioselective [5+4] Annulations of ortho-Quinone Methides and Vinylethylene Carbonates

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Org. Chem. Front., 2020, Accepted Manuscript
DOI: 10.1039/D0QO00128G, Research Article
Chao Xia, Dong-Chao Wang, Gui-Rong Qu, Hai-Ming Guo
Highly enantioselective [5+4] annulations of ortho-quinone methides with vinylethylene carbonates were enabled by phosphine/palladium asymmetric cooperative catalysis for the first time. Efficient synthesis of various nine-membered benzo-heterocycles was achieved in...
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Mechanism and Origins of Stereo- and Enantioselectivities of Palladium-Catalyzed Hydroamination of Racemic Internal Allenes via Dynamic Kinetic Resolution: A Computational Study

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Org. Chem. Front., 2020, Accepted Manuscript
DOI: 10.1039/D0QO00174K, Research Article
Zhenzhen Wu, Mei Zhang, Yu Shi, Genping Huang
Density functional theory calculations have been performed to investigate the Pd-catalyzed hydroamination of racemic internal allenes with pyrazoles. The computations show that the originally proposed reaction mechanisms initiated by the...
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Catalyst-Controlled Formal [4+1] Annulation of N-Vinyl Fluorenone Nitrones and Allenoates to Prepare Spirofluorenylpyrrolines

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Org. Chem. Front., 2020, Accepted Manuscript
DOI: 10.1039/D0QO00224K, Research Article
Cui Wei, Jin-Qi Zhang, Jia-Jie Zhang, Cui Liang, Dong-Liang Mo
We report a readily commercial Gimeracil-catalyzed formal [4+1] annulation approach for the synthesis of spirofluorenylpyrrolines in good yields with high diastereoselectivity from easily available N-vinyl fluorenone nitrones and allenoates. The...
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A Vinylogous Michael Reaction of 2-Furanones Dimers to α, β-Unsaturated Nitroolefins for Constructing Chiral γ, γ-Disubstituted Butenolides

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Org. Chem. Front., 2020, Accepted Manuscript
DOI: 10.1039/D0QO00376J, Research Article
Zhushuang Bai, Cairong Zhang, Yongyi Chen, Aiqin Liu, Xinyu Wang, Chuna Yan, Xuechao Liu, Xiaoru Zhang, Ying Li, Ye Yuan, Zemei Ge, Jingxiang Pang, Yongshuai Chai, Xin Wang, Runtao Li
An efficient bifunctional thiourea catalyzed asymmetric vinylogous Michael addition of 2-furanones dimers to α, β-unsaturated nitroolefins has been developed to give the functional chiral γ,γ-disubstituted butenolides in good yields (up...
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Rhodium(III)-catalyzed synthesis of 3-trifluoromethylindanones from N-Methoxybenzamides via C-H activation and Claisen/Retro-Claisen reaction

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Org. Chem. Front., 2020, Accepted Manuscript
DOI: 10.1039/D0QO00330A, Research Article
Satyasheel Sharma, Bharatkumar Chaudhary, Neeraj Kulkarni
The Rhodium(III)-catalyzed reaction of N-methoxybenzamides as a directing group with β-trifluoromethyl-α,β-unsaturated ketones is reported. The reaction involved sp2 C−H activation, followed by Claisen condensation involving C-N bond cleavage to form...
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Targeted Isolation of Two Disesquiterpenoids Macrocephadiolides A and B from Ainsliaea macrocephala using Molecular Networking-based Dereplication Strategy

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Org. Chem. Front., 2020, Accepted Manuscript
DOI: 10.1039/D0QO00030B, Research Article
Yong-Mei Ren, Shuaizhen Zhou, Tian Zhang, Meijia Qian, Rui Zhang, Sheng Yao, Hong Zhu, Chunping Tang, Ligen Lin, Yang Ye
A molecular networking-based dereplication strategy was applied to the phytochemical investigation of Ainsliaea macrocephala, leading to the isolation of two novel disesquiterpenoids macrocephadiolides A (1) and B (2). Their structures,...
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