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Kinetic resolution of 1,1'-binaphthyl-2,2'-diamine derivatives by chiral calcium phosphate-catalyzed acylation

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00355A, Paper
Tatsuhiro Uchikura, Yuki Kanno, Yukino Fukuda, Mikoto Sato, Takahiko Akiyama
Chiral calcium phosphate-catalyzed kinetic resolution of BINAM derivatives.
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Rapid in situ generation of 2-(halomethyl)-5-phenylfuran and nucleophilic addition in a microflow reactor

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00358F, Paper
Open Access
Yuma Matsuura, Shinichiro Fuse
Various 2,5-disubstituted furans were synthesized via 5-substituted 2-halomethylfurans using microflow technology.
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On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00241E, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Julia A. Turner, Hendrik Zipse, Mark S. Taylor
Computational analysis of the HAT-induced expulsion of carboxylic acids from monoacylated pyranosides implicates concerted elimination through a hydrogen-bonded transition state.
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Use of ionic liquids in amidation reactions for proteolysis targeting chimera synthesis

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00304G, Paper
Michela Eleuteri, Jenny Desantis, Gabriele Cruciani, Raimondo Germani, Laura Goracci
Selective degradation of disease-causing proteins using proteolysis targeting chimeras (PROTACs) has gained great attention, thanks to its several advantages over traditional therapeutic modalities.
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An efficient synthesis of mono-, di-, and tri-substituted 1,3-thiazoles employing functionalized thioamides as thiocarbonyl precursors

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00229F, Paper
Kalleshappa Sheela, Chikkappaiahnayaka Santhosh, Krishna Ravi Singh, Kalleshappa Sharath, Maralinganadoddi P. Sadashiva
Herein, we report an efficient strategy to synthesize functionalized 1,3-thiazoles using alkyl 2-amino-2-thioxoacetates.
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Electrochemical and photochemical reaction of isatins: a decade update

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00202D, Review Article
Nandini M. Gotgi, J. Saurab Jain, Rita Pal, Debashis Ghosh
This review presents all the recent reports on electro- and photochemical reactions of isatins over the last decade.
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A rhodium-catalyzed cascade C–H activation/annulation strategy for the expeditious assembly of pyrrolidinedione-fused 1,2-benzothiazines

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00193A, Paper
Yinsong Wu, Guanghao Shi, Yanan Liu, Yangzilin Kong, Mengdi Wu, Demao Wang, Xiaobing Wu, Yongjia Shang, Xinwei He
We have developed a cascade annulation strategy triggered by rhodium(III)-catalyzed C–H activation for the expeditious assembly of pyrrolidinedione-fused 1,2-benzothiazines from free NH-sulfoximines with maleimides under mild conditions.
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Generation of sulfones utilizing β-sulfinyl esters as masked aryl sulfinates under redox-neutral conditions

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00238E, Communication
Yixin Zhang, Zhu Yang, Hongjun Yang, Xuefeng Li, Lu Yang
A method for generation of SVI sulfones from β-sulfinyl esters (SIV) under transition-metal-free non-oxidative mild conditions is presented.
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Correction: Recent progress of core-substituted naphthalenediimides: highlights from 2010

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB90045F, Correction
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Sheshanath V. Bhosale, Sidhanath V. Bhosale, Suresh K. Bhargava
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HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-b]quinolines & related natural products

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00414K, Paper
Auqib Rashid, Waseem I. Lone, Preeti Dogra, Showkat Rashid, Bilal A. Bhat
An expeditious metal free C-3 alkylation of indoles and its NIS-mediated deviation to indolo[2,3-b]quinolines is reported. Applications of these strategies in accessing bioactive natural products have also been demonstrated.
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A copper-catalyzed asymmetric Friedel–Crafts hydroxyalkylation of pyrazole-4,5-diones with 5-aminoisoxazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00322E, Communication
Siyu Gao, Xiang Sun, Sijie Peng, Zhenggen Zha, Qi Sun, Zhiyong Wang
An asymmetric Friede-Crafts hydroxyalkylation reaction was developed under the catalysis of chiral copper complexes. A variety of pyrazolone derivatives were obtained with excellent yields and enantioselectivities.
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Copper-catalyzed ortho-thiocyanation of aromatic amines

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00137K, Communication
Monak Patel, Nitish Kumar, Hussain Bhukya, Bharatkumar Z. Dholakiya, Togati Naveen
Here, we described an efficient ortho- C(sp2)-H thiocyanation of anilines for the synthesis of aryl thiocyanates. This protocol tolerates a variety of aromatic amines to provide the desired products in good to excellent yields.
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Synthesis of fluorescent 5-heteroarylpyrimidine-containing oligonucleotides via post-synthetic trifluoromethyl conversion

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00402G, Paper
Yuta Ito, Hisato Tanaka, Ayana Murakami, Yasufumi Fuchi, Yoshiyuki Hari
5-(Benzimidazol-2-yl)- and 5-(benzothiazol-2-yl)-pyrimidine bases-modified oligonucleotides were prepared by post-synthetic trifluoromethyl conversion and their fluorescence properties were measured.
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Chemoenzymatic total synthesis of rotigotine via IRED-catalyzed reductive amination

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00072B, Communication
Dongyu Tang, Yaqing Ma, Jinping Bao, Shushan Gao, Shuli Man, Chengsen Cui
An engineered imine reductase (IRED) was developed specifically for 2-tetralone substrate, and utilized in the total synthesis of rotigotine.
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Rh(III)-catalysed C-H annulation of cis-stilbene acids with 2-diazo-1,3-diketones: A facile access to 6,7-dihydrobenzofuran-4(5H)-one and α-pyrone scaffolds

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00151F, Paper
Shankaraiah Nagula, Mary Sravani Galla, Nandini B. Kale, Akshay Kumawat, Darshana Bora
An efficient Rh(III)-catalysed C-H functionalization, tandem annulation of cis-stilbene acids using 2-diazo-1,3-diketones was devised. The protocol has solely afforded 6,7-dihydrobenzofuran-4(5H)-ones using alicyclic diazocarbonyls via decarbonylation and α-pyrones with aliphatic diazo...
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The synthesis of alk-2-ynl Weinreb amides via Pd/Cu-catalysed oxidative carbonylation of terminal alkynes

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00290C, Paper
Bharati Mourya, Sandip T. Gadge, Bhalchandra M. Bhanage
Synthesis of alk-2-ynl-Weinreb amides via Pd-catalyzed oxidative carbonylation of terminal alkynes and N,O-dimethylhydroxylamine hydrochloride at room temperature under low CO/O2 pressure is reported for the first time.
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DMSO promoted catalyst-free oxidative C–N/C–O couplings towards synthesis of imidazoles and oxazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00383G, Paper
Debasish Bera, Rajib Sarkar, Tiyasa Dhar, Pinaki Saha, Prasanta Ghosh, Chhanda Mukhopadhyay
Dimethyl sulfoxide (DMSO)-promoted catalyst-free oxidative C–N coupling and C–O coupling under oxidant-free conditions are outlined.
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Synthesis of Asp-based lactam cyclic peptides using an amide-bonded diaminodiacid to prevent aspartimide formation

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00472H, Communication
Wen-Jie Li, Jun-You Chen, Hui-Xia Zhu, Yi-Ming Li, Yang Xu
A diaminodiacid (DADA) containing an amide bond can be used in Fmoc solid-phase peptide synthesis (SPPS) of an Asp-based lactam cyclic peptide with no aspartimide formation.
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Synthesis of alkenylphosphine oxides via Tf2O promoted addition–elimination of ketones and secondary phosphine oxides

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00318G, Communication
Jiangkai Ma, Lianjie Wang, Anjiang Qiao, Zhongxian Li, Fengqian Zhao, Junliang Wu
An efficient method for the synthesis of alkenylphosphine oxides via the addition-elimination of SPOs to ketones has been developed. The reaction exhibits good yields and compatibility. Several conversions have also proven the value of this method.
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DFT investigation of the DDQ-catalytic mechanism for constructing C–O bonds

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00346B, Paper
Xiu-Fang Zheng, Da-Gang Zhou, Li-Jun Yang
The DDQ-catalytic mechanisms for constructing C–O bonds via H2O and CH3OH as oxygen sources have been investigated with DFT.
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Electrochemical nickel-catalyzed cross-coupling of glycosyl thiols with preactivated phenols and ketones

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00442F, Communication
Fuxin Li, Hui Liu, Wanyu Xing, Qingju Zhang, Liming Wang
Here we report an efficient electrochemical nickel-catalyzed cross-coupling reaction for the synthesis of S-glycosides from preactivated phenols and ketones.
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Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00393D, Paper
Rasmita Barik, Samik Nanda
Naturally occurring sesquiterpenes having humulane frameworks are structurally intriguing and possess significant biological profiles.
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Structural flexibility of favipiravir and its structural analogues in solutions: experimental and computational insight

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00404C, Paper
Tatiana P. Gerasimova, Almaz A. Zagidullin, Anastasiia N. Nikolaeva, Robert R. Fayzullin, Aliya M. Saitova, Vasili A. Miluykov, Stefan Grimme, Sergey A. Katsyuba
Keto-enol transformations of 6-R-3-hydroxy-2-pyrazinecarboxamides in solutions are accompanied by deprotonation of enol tautomers and the formation of corresponding anionic species. The key factors determining these processes have been identified.
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Total synthesis of diplofuranone A and diapolic acid A

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00433G, Communication
Dattatraya H. Dethe, Vimlesh Kumar, Nagabhushana C. Beeralingappa
The first and concise syntheses of the anticancer agent diplofuranone A and the fatty acid-derived metabolite diapolic acid A have been demonstrated using easily accessible and commercially available starting materials.
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Stereoselective Synthesis of gem-Dihalopiperidines via Halo-Aza-Prins Cyclization Reaction: Access to Piperidin-4-ones and Pyridines

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00338A, Paper
Anil Kumar Saikia, Surjya Kumar Bora, Subhamoy Biswas, Bipin Kumar Behera
An efficient methodology for the synthesis of 4,4-dihalopiperidine derivatives has been developed from N-(3-halobut-3-en-1-yl)-4-methylbenzenesulfonamide and aldehyde catalyzed by In(OTf)3 in excellent yields. The reaction involves an initial formation of six...
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Reduction of sulfoxides catalyzed by the commercially available manganese complex MnBr(CO)5

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00204K, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Daniel Leal Lourenço, Ana Cristina Fernandes
A new methodology for the reduction of a wide variety of aliphatic and aromatic sulfoxides catalyzed by the air-stable, cheap and commercially available manganese catalyst MnBr(CO)5 with excellent yields is...
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Asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A

Org. Biomol. Chem., 2024, 22,2958-2962
DOI: 10.1039/D4OB00104D, Communication
Ying Sun, Shaomin Fu, Bo Liu
The asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A is presented.
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Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Org. Biomol. Chem., 2024, 22,2916-2947
DOI: 10.1039/D3OB01904G, Review Article
Swadhin Swaraj Acharya, Sagarika Patra, Rojalini Maharana, Manaswini Dash, Liza Mama Barad, Bibhuti Bhusan Parida
In recent years, the maleimide scaffold has received a great deal of attention in C–H activation.
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Vinylogous and stereoselective domino synthesis of pyrano[2,3-c]pyrroles from alkylidene meldrum's acids

Org. Biomol. Chem., 2024, 22,2948-2952
DOI: 10.1039/D4OB00233D, Communication
Mariia Savchuk, Giang Vo-Thanh, Sylvain Oudeyer, Hélène Beucher, Jean-François Brière
An expeditious diatereoselective synthesis of pyrano[2,3-c]pyrroles thanks to a domino Vinylogous aza-Michael-Aldol-Cyclocondensation (aza-VMAC) reaction to alkylidene Meldrum's acid derivatives.
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Selective synthesis of an elusive C-functional bis-cyclam and study of its inhibition of the CXCR4 chemokine receptor

Org. Biomol. Chem., 2024, 22,3059-3067
DOI: 10.1039/D3OB02050A, Paper
Marie M. Le Roy, Sandra Claes, Nathalie Saffon-Merceron, Dominique Schols, Thibault Troadec, Raphaël Tripier
A rare example of C,C'-linked bis-cyclam has been synthesized with controlled manner in mild conditions thanks to the “bis-aminal” tool, and its good CXCR4-recognition properties could be demonstated in vitro.
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Hydrosilylation of nitriles and tertiary amides using a zinc precursor

Org. Biomol. Chem., 2024, 22,3053-3058
DOI: 10.1039/D4OB00161C, Paper
Ravi Kumar, Rohan Kumar Meher, Himadri Karmakar, Tarun K. Panda
A competent and selective hydrosilylation of nitriles and tertiary amides catalyzed by zinc bis(hexamethyldisilazide) [Zn(HMDS)2] under solvent-free and mild conditions are reported, as a sustainable and desirable alternative to existing methods.
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Albumin–ruthenium catalyst conjugate for bio-orthogonal uncaging of alloc group

Org. Biomol. Chem., 2024, 22,2992-3000
DOI: 10.1039/D4OB00234B, Paper
Kimberly S. Taylor, Madison M. McMonagle, Schaelee C. Guy, Ariana M. Human-McKinnon, Shumpei Asamizu, Heidi J. Fletcher, Bradley W. Davis, Takashi L. Suyama
An organo–ruthenium catalyst conjugated to albumin efficiently unmasks an alloc group under physiologically relevant conditions.
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Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams

Org. Biomol. Chem., 2024, 22,2985-2991
DOI: 10.1039/D4OB00285G, Paper
Open Access
Zhongzhen Yang, Marion Arnoux, Damien Hazelard, Owen R. Hughes, Joe Nabarro, Adrian C. Whitwood, Martin A. Fascione, Christopher D. Spicer, Philippe Compain, William P. Unsworth
New Successive Ring Expansion (SuRE) protocols are described for use on unreactive lactams, as well as iminosugar derived lactams.
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Photogenerated chlorine radicals activate C(sp3)–H bonds of alkylbenzenes to access quinazolinones

Org. Biomol. Chem., 2024, 22,2968-2973
DOI: 10.1039/D4OB00129J, Communication
Xin-Yao Pan, Gui-Xia Sun, Fang-Ping Huang, Wen-Jian Qin, Qing-Hu Teng, Kai Wang
An Fe-catalyzed visible-light induced condensation of alkylbenzenes with anthranilamides has been developed.
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A phosphamide nucleotide analog: a substrate for polymerase synthesis of DNA

Org. Biomol. Chem., 2024, 22,2963-2967
DOI: 10.1039/D4OB00089G, Communication
Jiong Meng, Qiaqia Guo, Xiaona Zhai, Song Yang, Shuai Wang, Pengcheng Wang, Debin Ji
A phosphamide nucleotide analog (dNTPγNH2) exhibited higher stability than dNTPs and can be recognized by DNA polymerases in PCR.
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Synthesis of alkynyl sulfides via base-promoted nucleophilic ring-opening of α-bromostyrene sulfonium salt

Org. Biomol. Chem., 2024, 22,2953-2957
DOI: 10.1039/D4OB00203B, Communication
Junqi Zhou, Ziyu Wang, Hanmiao Xu, Mengke Su, Jian Wen
An effective method for synthesizing various alkynyl sulfides has been developed using tetramethylene sulfoxide as a sulfur source through base-promoted nucleophilic ring-opening reactions.
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Identification and quantification of local antiaromaticity in polycyclic aromatic hydrocarbons (PAHs) based on the magnetic criterion

Org. Biomol. Chem., 2024, 22,3035-3044
DOI: 10.1039/D4OB00114A, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Erich Kleinpeter, Andreas Koch
The ring current effect of entirely and partly (anti)aromatic PCHs are calculated and employed to visualize, qualify and quantify existing (anti)aromaticity, especially to decide unequivocally between PAHs and PAAHs.
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Palladium-catalyzed (Z)-selective allylation of phosphine oxides with vinylethylene carbonates to construct phosphorus allyl alcohols

Org. Biomol. Chem., 2024, 22,3068-3072
DOI: 10.1039/D4OB00354C, Paper
Hua Huang, Yi-Qi Wu, Lu-Yao Han, Lu Jiang, Zhuo-Zhuo Zhang, Xiang Zhang, Bo Han, Wei Huang, Jun-Long Li
A general and efficient method for the highly stereoselective synthesis of (Z)-phosphorus allylalcohols has been developed using the Pd-catalyzed cross-coupling of phosphine oxides with vinylethylene carbonates.
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Stereoselective synthesis of (R)- and (S)-1,2-diazetidine-3-carboxylic acid derivatives for peptidomimetics

Org. Biomol. Chem., 2024, 22,2974-2977
DOI: 10.1039/D4OB00278D, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Matthew Nutter, Henry Stone, Michael Shipman, Stefan Roesner
Stereoselective synthesis of both enantiomers of orthogonally protected 1,2-diazetidine-3-carboxylic acid (aAze) from homochiral glycidol and its application in peptidomimetics.
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Additive-free oxychlorination of unsaturated C–C bonds with tert-butyl hypochlorite and water

Org. Biomol. Chem., 2024, 22,3080-3085
DOI: 10.1039/D4OB00003J, Paper
Duyi Shen, Chaoyue Sun, Yun Han, Zhen Luo, Ting Ren, Qin Zhang, Wenting Huang, Jianru Xie, Ying Jia, Mianran Chao
A facile oxychlorination of various alkynes and alkenes with tBuOCl as an alternative chlorine source and H2O as a green oxygen source.
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Selective enhancement of (6–4) photoproduct formation in dithymine dinucleotides driven by specific sugar puckering

Org. Biomol. Chem., 2024, 22,3025-3034
DOI: 10.1039/D4OB00279B, Paper
Jouda Jakhlal, Clément Denhez, Stéphanie Coantic-Castex, Agathe Martinez, Dominique Harakat, Thierry Douki, Dominique Guillaume, Pascale Clivio
Evidence is presented that (6–4) photoproduct formation between two thymine residues in dinucleotide analogues is significantly and specifically enhanced when the 5''- and 3''-end sugar puckering are mainly north and south, respectively.
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Iron-catalyzed selective construction of indole derivatives via oxidative C(sp3)–H functionalization of indolin-2-ones

Org. Biomol. Chem., 2024, 22,3073-3079
DOI: 10.1039/D4OB00133H, Paper
Wei Chen, Lang-Qi Wen, Xiao-Bing Lu, Hui Zhou
We have developed a clean and efficient iron-catalyzed C(sp3)–H functionalization of indolin-2-ones for the chemodivergent synthesis of value-added indole derivatives, including isatins, and symmetrical and non-symmetrical isoindigos.
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Direct access to pyrrole anhydrides via oxidative self-coupling of pyrrole carboxaldehydes

Org. Biomol. Chem., 2024, 22,3045-3052
DOI: 10.1039/D4OB00052H, Paper
Surabhi Panday, Tapas Maity, Pratibha Bhatti, Joydev K. Laha
An elegant synthesis of pyrrole-2-carboxylic acid anhydrides from pyrrole-2-carboxaldehydes using TBAI as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant is described herein.
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Photochromism of phenazine-2,3-diol derivatives through excited state intermolecular proton transfer based on keto–enol tautomerization

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00387J, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Kazuki Ohira, Kumpei Kozuka, Naoki Kaneda, Masahiro Yamamoto, Keiichi Imato, Yousuke Ooyama
It was found that phenazine-2,3-diol derivatives exhibit photochromism through excited state intermolecular proton transfer (ESInterPT) processes based on keto–enol tautomerization.
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Charge-transfer inclusion complex formation of the tropylium cation with prism[6]arenes

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00423J, Communication
Guojiao Zhang, Channi Cheng, Zhengxiang Li, Dezhi Zhao, Chengyou Han
We report that charge-transfer (CT) inclusion complexes were formed between prism[6]arenes and tropylium cation. Additionally, the CT complex showed Cl/Ag+ responsiveness which can be easily monitored by the naked eye.
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BBr3-mediated dearomative spirocyclization of biaryl ynones: facile access to spiro[5.5]dienones

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00274A, Communication
Gaurav Jaiswal, Subhas Chandra Pan
BBr3 mediated dearomative spirocyclization of biaryl ynones has been reported for the direct synthesis of spiro[5.5]dienones with a tri-substituted double bond.
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Nickel-catalysed regio- and stereoselective hydrocyanation of alkynoates and its mechanistic insights proposed by DFT calculations

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00380B, Communication
Shigeru Arai, Koichi Nakazawa, Xiao-Fei Yang, Masaya Nakajima, Shinji Harada, Atsushi Nishida
This work discloses the origin of regio- and stereoselectivity of hydrocyanation of alkynoates.
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Exploring the mechanism of the reductive amination of acetophenones via Borch approach: the role of the acid catalyst

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00160E, Paper
João Pedro Albuquerque Souza, Amanda Krauskopf Jacobs, Leandro Piovan, Renan Borsoi Campos
The energetic viability of several mechanistic variations of the reductive amination of acetophenones via the Borch approach was reexamined through density functional theory calculations. The crucial involvement of the acid...
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3-Halo-5,6-dihydro-4H-1,2-oxazine N-oxides as synthetic equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00391H, Communication
Alexander A. Lukoyanov, Svetlana A. Aksenova, Andrey A. Tabolin, Alexey Yu. Sukhorukov
3-Halo-1,2-oxazine N-oxide derivatives act as surrogates of vinyl nitrile oxides in tandem [3 + 2]-cycloaddition/[3 + 2]-cyclofragmentation with arynes leading to benzisoxazoles.
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Cu(OTf)2/HFIP catalyzed regioselective cycloisomerization of indole-C3-functionalized alkynols to carbazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00421C, Communication
Srinivasarao Yaragorla, Tabassum Khan, Sayonika Chakroborty
We report here a simple and atom economic cycloisomerization reaction of indole-tethered alkynols for constructing diverse carbazoles via 1,2-alkly migration using Cu(OTf)2/HFIP as the excellent promoter system.
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