Article
Chemistry, Multidisciplinary
Xuchao Wang, Jing Xue, Zi-Qiang Rong
Summary: This study reports a highly efficient catalyst-tuned regio- and enantioselective hydroalkylation reaction for the divergent synthesis of chiral C2- and C3-alkylated pyrrolidines. The reaction uses readily available catalysts and chiral ligands to synthesize enantioenriched compounds with excellent regio- and enantioselectivity. It also demonstrates compatibility with complex substrates derived from a series of drugs and bioactive molecules, providing a distinct entry to more functionalized chiral N-heterocycles.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Swetha Jos, Connor Szwetkowski, Carla Slebodnick, Robert Ricker, Ka Lok Chan, Wing Chun Chan, Udo Radius, Zhenyang Lin, Todd B. Marder, Webster L. Santos
Summary: A transition metal-free, regio- and stereo-selective, phosphine-catalyzed method for the synthesis of (E)-1-boryl-1,3-enynes has been reported in this paper. The reaction proceeds with high selectivity for boron addition to the external carbon of the 1,3-diyne framework.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Jian-Shu Wang, Yi Na, Jun Ying, Xiao-Feng Wu
Summary: The cobalt-catalyzed regioselective cycloaddition of diynes and alkynes allows for the construction of structurally diverse substituted 1,3-dihydroisobenzofurans with excellent yields and regioselectivities.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Organic
Chao Yang, Dong-Ting Dai, Huan-Xuan Lu, Feng-Lian Zhang, Yao Fu, Yun-He Xu
Summary: Unprecedented palladium-catalysed regio- and stereo-selective coupling reactions of homoallenylboronates with various reactants in aqueous solution resulted in high yields of products with specific stereoselectivity, demonstrating the potential of homoallenylboronates as powerful and flexible platform molecules for the formation of complex 1,3-dienyl compounds.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Kun Cui, Yan-Lin Li, Gongqiang Li, Ji-Bao Xia
Summary: A new regio- and stereoselective reductive coupling of alkynes and crotononitrile has been developed using visible light organophotoredox cobalt dual catalysis, resulting in the synthesis of enantioenriched homoallylic nitriles with stereodefined trisubstituted alkene.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Jianwen Jin, Andres Felipe Leon Rojas, Yichao Zhao, Sara Helen Kyne, Bo Xia, Bingwei Zhong, Philip Wai Hong Chan
Summary: This study presents a synthetic method for efficiently preparing (E)-3-arylazoindoles, which does not require the exclusion of air or moisture and can be conducted under mild reaction conditions. The suggested mechanistic pathway of the azo coupling reaction reveals the unique electrophilic behavior of α-diazocarbonyl compounds. Experimental studies provide insights into the preferential generation of a (1H-indol-3-yl)gold species and its impact on the regio- and chemoselectivity of the products. The utility of this synthetic method has been demonstrated in the synthesis of specific molecules, molecular switch assembly, and late-stage functionalization of biologically relevant molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Dat Phuc Tran, Yuki Sato, Yuki Yamamoto, Shin-ichi Kawaguchi, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa
Summary: The study developed a method that can generate pentavalent and trivalent phosphorus-centered radicals simultaneously by homolytic cleavage of the P-V(O)-P-III bond, enabling the phosphinylphosphination of terminal alkynes. This method exhibits high regio- and stereoselectivity and can be applied to a wide range of terminal alkynes.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yu-Qing Li, Guang Chen, Shi-Liang Shi
Summary: This Ni-catalyzed three-component coupling reaction provides a general synthetic approach to 1,4-disubstituted homoallylic alcohols, which were previously difficult to access. The reaction is regioselective, trans-selective, and can tolerate highly base-sensitive functional groups under neutral conditions.
Article
Chemistry, Multidisciplinary
Rupali S. S. Bhise, Prashant V. V. Ghorpade, Viral R. R. Mehta, Ganapati S. S. Shankarling
Summary: We have prepared a commercially viable Deep Eutectic Solvent (DES) based on Choline Chloride-Urea-copper acetate for the first time. It mediates the homocoupling of terminal alkynes, using air as an oxidant. Water is the only by-product of the entire process. The method avoids ligands, bases, oxidants, and costly palladium catalysts, making the process greener than ever. The DES can be reused at least three times without significantly affecting the reaction yield. The key features of the protocol, including ambient reaction temperatures, lesser use of conventional organic solvents, higher yields, and easy product isolation, qualify the process as a green one.
Article
Chemistry, Organic
Peng Zhou, Shangwei Feng, Huihua Qiu, Jiantao Zhang
Summary: This method provides a practical and environmentally friendly approach for the synthesis of 1-iodoalkynes, featuring simple operation, high efficiency, broad functional-group tolerance, and mild reaction conditions. The use of dioxygen in these reactions avoids the addition of hazardous or toxic oxidants, making it a safe and sustainable option for chemical synthesis.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jie Tang, Zhen-Hui Yan, Gu Zhan, Qian-Qian Yang, Ying-Ying Cheng, Xiang Li, Wei Huang
Summary: This study discloses for the first time the visible-light-mediated sequential Wolff rearrangement and Staudinger cycloaddition, which utilize in situ generated ketenes and pyrazolone ketimines to assemble valuable spiro-pyrazolone-beta-lactams. This powerful approach exhibits high yield, good substrate tolerance, and gram-scale capacity, providing straightforward access to multisubstituted pyrazole-morpholine skeletons.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Multidisciplinary Sciences
Yingzhuang Xu, Songyi Li, Huayi Fang
Summary: This article reports the synthesis of a rare coplanar dinuclear hydroxycarbonylcobalt(III) complex and demonstrates that the Co - carboxylate bonds can be easily cleaved, leading to the formation of oxalic acid. The authors also achieved the direct production of oxalic acid from CO and H2O using this complex as a catalyst, with high selectivity and atom economy.
NATURE COMMUNICATIONS
(2023)
Article
Polymer Science
Sentaro Okamoto, Takeshi Yamada, Takaya Uchida, Nana Kikuta, Yu-ya Kimura
Summary: This article discusses the application of a low-valent titanium reagent in the McMurry coupling polymerization and [2+2+2] cycloaddition polymerization of aryl dialdehyde and aromatic diyne monomers. Additionally, a low-valent titanium mediated dual-mode coupling copolymerization of aryl dialdehyde and alkynylaldehyde monomers via concurrent McMurry olefination and alkyne cyclotrimerization reactions is proposed.
Article
Chemistry, Physical
Sumit Roy, Radha Krishna Kashyap, Pramod P. Pillai
Summary: This study explores the use of nanoparticles as building blocks in a dynamic self-assembly process that is responsive to multiple stimuli, with the solvent playing an important role. The hygroscopic nature of dimethyl sulfoxide (DMSO) allows for the autonomous dissolution of water into the dispersion of thymine-functionalized gold nanoparticles (Thy-AuNPs), triggering the self-assembly step. Sunlight is utilized as a fuel to input thermal energy into the solvent-mediated dynamic self-assembly process of the nanoparticles, leading to the disassembly step.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Organic
Uladzimir S. Masiuk, Yaroslav V. Faletrov, Dzmitry G. Kananovich, Iryna Mineyeva
Summary: The stereodivergent synthesis of cis- and trans-2,6-disubstituted tetrahydropyrans (THPs) has been achieved through the oxa-Michael cyclization of (E)-zeta-hydroxy alpha,beta- unsaturated esters promoted by sodium hexamethyldisilazide. The reaction at low temperature (-78 degrees C) yields the thermodynamically favored trans-THPs with high stereoselectivity, while the reaction at room temperature does not produce the desired cis-THPs as major products and has poor stereocontrol. The addition of tetramethylethylenediamine significantly improves the stereochemical outcome of the room-temperature cyclization and allows for high cis-selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pierre Hansjacob, Frederic R. Leroux, Vincent Gandon, Morgan Donnard
Summary: The palladium-catalyzed silylcyanation of ynamides is highly selective, producing exclusively tetrasubstituted 2-aminoacrylonitriles derivatives. The stereoselectivity is directly controlled by the nature of the substituent at the beta-position of the ynamide. The reaction is tolerant of various functional groups and provides a general method to access fully substituted 2-aminoacrylonitriles. The mechanism of this intriguing transformation is elucidated by computational study, and the range of 2-aminoacrylonitriles is expanded through postfunctionalization using the newly installed vinylsilane functionality.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xu Han, Quentin Gaignard-Gaillard, Pascal Retailleau, Vincent Gandon, Arnaud Voituriez
Summary: The cycloisomerization of N-tethered indole and dihydropyrrole-arylpropargyl substrates into complex polycycles was investigated using gold(i) catalysis. Enantioselectivities up to 93% ee were achieved in the asymmetric version of this process. DFT calculations provided insights into the reactivity observed for the formation of such complex molecular frameworks.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Vandana Jaiswal, Mangilal Godara, Dinabandhu Das, Vincent Gandon, Jaideep Saha
Summary: A highly regioselective domino skeletal-expansion process has been developed to transform 2-aminothiazolidinone into six-membered S,N-heterocycle, utilizing TMS-azide in HFIP at ambient temperature. The C2 tertiary amine functioned as a latent reactive group, allowing relay substitution with azide and subsequent ring-expansion under metal/acid free-conditions. The strategy showed potential for synthesis of Se,N-heterocycles and late-stage drug-modification.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Marie Vayer, Sophie Rodrigues, Solene Miaskiewicz, David Gatineau, Yves Gimbert, Vincent Gandon, Christophe Bour
Summary: This study describes a gallium-catalyzed C-H propargylation of electron-rich arenes using bromoallenes. By using K2CO3 as a base, the side hydroarylation process catalyzed by adventitious protons from the solvent can be bypassed, and the GaCl3/K2CO3 system is found to trigger a wide range of reactions.
Article
Chemistry, Multidisciplinary
Juba Ghouilem, Sokna Bazzi, Nicolas Grimblat, Pascal Retailleau, Vincent Gandon, Samir Messaoudi
Summary: This study presents a novel method for the Pd(ii)-catalyzed arylation of 3-aminosugars using a transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine is transformed into an azide function, which is further utilized in a CuAAC reaction to generate complex substituted C3-triazolo C-glycosides with high yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Capucine Mahe, Olivier Blacque, Gilles Gasser, Vincent Gandon, Kevin Cariou
Summary: The first synthesis of various N-metallocenyl ynamides has been achieved, along with the development of two strategies for the oxidative cyclization of N-ferrocenyl ynamide into ansa[3]-ferrocenylamide. The mechanism for the iodine(III)-triggered transformation has been investigated using DFT calculations, revealing a concerted iodination deprotonation step.
Article
Chemistry, Multidisciplinary
Audrey Mauger, Maxime Jarret, Aurelien Tap, Remi Perrin, Regis Guillot, Cyrille Kouklovsky, Vincent Gandon, Guillaume Vincent
Summary: We synthesized highly strained pentacyclic caged framework of mavacuran alkaloids and successfully achieved the concise total synthesis of C-fluorocurine, C-profluorocurine, C-mavacurine, normavacurine, 16-epi-pleiocarpamine and taberdivarine H. A strategy involving late-stage Michael addition and intermolecular 1,4-addition reactions was designed. The first total syntheses of C-profluorocurine and C-fluorocurine were achieved through dihydroxylation of C-mavacurine and a pinacol rearrangement, respectively.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Vivek W. Bhoyare, E. Daiann Sosa Carrizo, Chetan C. Chintawar, Vincent Gandon, Nitin T. Patil
Summary: In this study, we present a ligand-enabled gold (Au) catalyzed Heck reaction using Au(I)/Au(III) redox catalysis. For the first time in gold chemistry, essential organometallic steps such as migratory insertion and s-hydride elimination have been achieved in a catalytic manner. This methodology not only overcomes the limitations of previous transition metal-catalyzed Heck reactions, such as the need for specialized substrates and the formation of a mixture of regioisomeric products due to undesirable chain-walking, but also provides complementary regioselectivity compared to other transition metal catalysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Stephanie Solier, Sebastian Mueller, Tatiana Caneque, Antoine Versini, Arnaud Mansart, Fabien Sindikubwabo, Leeroy Baron, Laila Emam, Pierre Gestraud, G. Dan Pantos, Vincent Gandon, Christine Gaillet, Ting-Di Wu, Florent Dingli, Damarys Loew, Sylvain Baulande, Sylvere Durand, Valentin Sencio, Cyril Robil, Francois Trottein, David Pericat, Emmanuelle Naeser, Celine Cougoule, Etienne Meunier, Anne-Laure Begue, Helene Salmon, Nicolas Manel, Alain Puisieux, Sarah Watson, Mark A. Dawson, Nicolas Servant, Guido Kroemer, Djillali Annane, Raphael Rodriguez
Summary: Inflammation is a complex physiological process that involves immune cells clearing sources of injury. Excessive inflammation is associated with infection and several diseases. The cell surface glycoprotein CD44 mediates the uptake of metals, including copper, and affects the metabolic and epigenetic states involved in inflammation.
Article
Chemistry, Physical
Arghadip Ghosh, Nicolas Grimblat, Somratan Sau, Arijit Saha, Vincent Gandon, Akhila K. Sahoo
Summary: This article presents a Pd-(II)-catalyzed direct difunctionalization of two C-(sp(3))-H bonds of aliphatic carboxylic acid derivatives using bifunctional reagents (BFRs) of the 2-iodobenzoic acid series. Various directing groups, ligands, bases, and co-oxidants are employed to facilitate the reaction, leading to the formation of benzo-fused peripheral-substituted caprolactones. Mechanistic studies provide insights into the crucial steps involved in the transformation. The versatility of the complex molecular entities is also showcased.
Article
Chemistry, Multidisciplinary
Arghadip Ghosh, Koneti Kondalarao, Arijit Saha, Vincent Gandon, Akhila K. Sahoo
Summary: A tandem three-component C-H bond addition involving the activation of an inert C(sp(3))-H bond is reported. The reaction enables the direct regioselective synthesis of 1,2-difunctionalized arenes. Mechanistic studies reveal the reaction pathway.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Junqiang Wei, Vincent Gandon, Ye Zhu
Summary: Synthetic application of asymmetric catalysis requires strategic alignment of bond construction and chiral target molecule creation. Remote desymmetrization offers advantages in spatial decoupling of catalytic transformation and generation of stereogenic element. However, this spatial separation presents challenges for chiral catalysts to discriminate distant enantiotopic sites several bonds away from a prochirality center.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Somratan Sau, Kallol Mukherjee, Koneti Kondalarao, Vincent Gandon, Akhila K. Sahoo
Summary: A chiral sulfoximine-enabled Ru-(II)-catalyzed asymmetric C-H activation/functionalization process has been developed for the synthesis of dihydrobenzofuran- or indoline-fused isoquinolinones with a tertiary or quaternary stereocenter. The method achieves high yields and enantioselectivities (up to 97:3 enantiomeric ratio) and allows for the recovery and reuse of the chiral sulfoxide precursor.
Article
Chemistry, Multidisciplinary
Jiaxin Tian, Marie Cordier, Christophe Bour, Audrey Auffrant, Vincent Gandon
Summary: The formation of a rare type of diphosphazenium cation is reported, achieved through a unique oxidative dealkylation of an iminophosphorane-phosphole using a silver(I) salt. DFT study reveals the low valent nature of the N(I) center in this compound.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Shengwen Yang, Solene Miaskiewicz, Christophe Bour, Aurelien Alix, Vincent Gandon
Summary: The overlooked pericyclic reaction between allyl alcohols and alkenes to form carbonyl compounds is analyzed, which combines the features of the Alder-ene reaction and the oxy-Cope rearrangement. This oxy-ene reaction could be involved in biosynthetic pathways.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
