Article
Chemistry, Organic
Ming Yang, Xue-Cen Xu, Yue Gong, Yu-Long Zhao
Summary: A rhodium-catalyzed coupling cyclization has been developed for the first time with isocyanides and 2-azidophenyloxyacrylates. This reaction allows for the divergent syntheses of two significant N-heterocycles in a single step from readily available starting materials.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Zheng-Yang Gu, Ji-Bao Xia
Summary: A efficient [3 + 1 + 1] cyclization of vinyl oxiranes has been developed for the synthesis of oxazolidinones via tandem palladium catalysis. This reaction provides an atom- and step-efficient strategy to produce oxazolidinones from readily available azides and carbon monoxide under mild additive- and base-free conditions. Mechanistic studies demonstrated that the reaction occurred through an in situ generated isocyanate intermediate.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Youliang He, Xiaoming Wang
Summary: A range of cyclic amidines were efficiently synthesized through an iridium-catalyzed deoxygenative reduction and one-pot cycloaddition reaction, providing a useful method for the late-stage diversification of complex structures containing lactam moieties.
Article
Chemistry, Organic
Ming Yang, Tao Liu, Yue Gong, Qing-Wen Ai, Yu-Long Zhao
Summary: A novel rhodium-catalyzed coupling-cyclization reaction between o-alkynyl/propargyl arylazides or o-azidoaryl acetylenic ketones and arylisocyanides has been developed. This reaction provides a new and simple strategy for the synthesis of 6H-indolo[2,3-b]quinolines, dibenzonaphthyridones, and dihydrodibenzo[b,g][1,8]-naphthyridines in a single step from readily available non-fused ring precursors, with only nitrogen generated as a by-product.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Ji Yang, Fabio G. Delolo, Anke Spannenberg, Ralf Jackstell, Matthias Beller
Summary: A new cobalt catalyst has been developed for the domino hydroformylation-reductive amination reaction of olefins, showing excellent regioselectivity under mild conditions. The Co-tert-BuPy-Xantphos catalyst is more selective than traditional cobalt(I) catalysts and even outperforms most known rhodium catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Matthew T. Whited, Wenlai Han, Helen J. Jin-Lee, Zach DiNardo, Emma Watson, Jia Zhang, Daniela Kohen
Summary: A cobalt silylene linkage enables metal/ligand cooperative activation and significantly improves the catalytic isocyanate generation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Debashish Mishra, Sagarika Rajkhowa, Prodeep Phukan
Summary: Unexpectedly, symmetrical sulfonyl guanidine was formed during the treatment of isonitriles with N,N-dibromoarylsulfonamides in absence of an external amine source. The interesting feature of this work is the switch of reactivity from the C-center to the N-center of isonitrile, where one molecule reacts via the C-end to produce an intermediate carbodiimide while the other molecule undergoes C N triple bond cleavage to act as an amine source with the intermediate.
Article
Chemistry, Multidisciplinary
Yevheniia Markushyna, Christoph M. Schuesslbauer, Tobias Ullrich, Dirk M. Guldi, Markus Antonietti, Aleksandr Savateev
Summary: Photocatalysis utilizes different colors of excitation light to selectively convert S-arylthioacetates into three different products. Factors such as negatively charged polyanion, positive valence band potential, intraband states, singlet oxygen sensitization, and multi-electron transfer contribute to this chromoselective conversion.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Matthias Elfinger, Timon Schoenauer, Sabrina L. J. Thomae, Robert Staeglich, Markus Drechsler, Mirijam Zobel, Juergen Senker, Rhett Kempe
Summary: The 3D metal catalyst developed here utilizes hydrogen as the reducing agent and easily handled ammonia dissolved in water as the nitrogen source for the synthesis of primary amines. The catalyst operates under mild conditions and outperforms commercially available noble metal catalysts. The key to its high activity is the unique support material it uses.
Article
Chemistry, Multidisciplinary
Timon Schoenauer, Sabrina L. J. Thomae, Leah Kaiser, Mirijam Zobel, Rhett Kempe
Summary: The development of C-N bond formation reactions is crucial in biology and chemistry, with recent progress in 3d metal catalysis showing unique selectivity patterns. By using a novel cobalt catalyst, a catalytic C-N bond formation reaction was successfully reported, utilizing abundant and low-cost starting materials for reductive alkylation.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Yu-Cheng Liu, Hang Shi
Summary: Functionalization of C(sp(3))-H bonds adjacent to a nitrogen atom using dual palladium catalysis provides access to α-branched amines with a broad scope. Mechanistic studies reveal an unusual Pd-0/Pd-II catalytic cycle involving oxidative cyclization and transmetallation.
Article
Chemistry, Multidisciplinary
Ai-Ran Liu, Lei Zhang, Jiao Li, Abudureheman Wusiman
Summary: A straightforward one-pot, multicomponent approach was developed to synthesize di- and tri-substituted N-sulfonyl formamidines from sulfonyl chlorides, NaN3, ethyl propiolate, and primary/secondary amines under mild conditions without catalysts or additives. Structural analysis showed the formation of E-syn/anti isomeric form for di-substituted sulfonyl formamidines, while tri-substituted analogues only formed E-isomers.
Article
Chemistry, Organic
Thao Nguyen Thanh Huynh, Khuyen Thu Nguyen, Mongkol Sukwattanasinitt, Sumrit Wacharasindhu
Summary: In this study, an electrochemical approach for the synthesis of guanidines from isothiocyanates and amines in a single reaction vessel is presented. The one-pot operation takes place in aqueous media with NaI serving as both the electrolyte and mediator. The process involves in situ generation of thiourea followed by electrolytic guanylation with amines. Under ambient temperature conditions, the formation of 30 different guanidine compounds with yields ranging from fair to excellent has been successfully demonstrated. This cost-effective and environmentally friendly synthesis method shows high tolerance towards various functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Thao Nguyen Thanh Huynh, Khuyen Thu Nguyen, Mongkol Sukwattanasinitt, Sumrit Wacharasindhu
Summary: In this study, an electrochemical method was developed for the synthesis of guanidines from isothiocyanates and amines in a single reaction vessel. The reaction takes place in aqueous media using an undivided cell setup with NaI as the electrolyte and mediator. The process involves the in situ generation of thiourea followed by electrolytic guanylation with amines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Julian Brueckel, Yannick Matt, Lisa Schmidt, Cornelia M. Mattern, Ute Schepers, Sonja Leopold, Martin Calkovsky, Dagmar Gerthsen, Stefan Braese
Summary: Porous organic materials obtained through the thermal decomposition of aromatic polyazide-containing precursors have been studied for their potential applications. These materials, known as Azide Thermolysis Frameworks (ATFs), exhibit self-inflating porous structures with tunable surface areas. The composition and properties of the ATFs are characterized using various techniques, and their potential for gas storage, separation, and catalysis is demonstrated.
Article
Chemistry, Multidisciplinary
Pei Xu, Yi-Ming Zhu, Xin-Yu Liu, Xiao-Zhou Zhou, Shun-Yi Wang, Shun-Jun Ji
Summary: The study has developed a method for the synthesis of pyrroloisoquinoline derivatives through the formation of two C-C bonds and one C-N bond via radical cascade cyclization in one step.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Jing-Jing Ai, Jian Li, Shun-Jun Ji, Shun-Yi Wang
Summary: This study reports a one-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions to afford selenocarbamates and allyl sulfone compounds. The method has advantages of being environmentally friendly, green, and having high atomic economy.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Xin-Yu Liu, Yan-Wei Zhao, Tian Jiang, Weidong Rao, Shun-Yi Wang
Summary: A new method for the synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF has been developed. This reaction is initiated by the trisulfur radical anion S-3(center dot-), generated in situ from K2(S) in DMF, without the need for transition-metal catalysis or other additives. In addition to forming two C-S bonds, the heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Ying Chen, Fei Wang, Bo-Xi Liu, Wei-Dong Rao, Shun-Yi Wang
Summary: A Ni(ii)-catalyzed reductive cross-coupling reaction has been developed for the synthesis of benzylic sulfides/selenides from oxalates and thiosulfonates/selenosulfonates under mild conditions. The use of oxalates prepared from corresponding alcohols as carbon radical precursors in the reaction provides an easy substrate availability and mild reaction conditions, offering a new method for the preparation of unsymmetrical sulfides/selenides with good functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Multidisciplinary Sciences
Fei Wang, Ying Chen, Weidong Rao, Lutz Ackermann, Shun-Yi Wang
Summary: In this work, the authors present a new method for the synthesis of disulfides through a reductive nickel-catalyzed cross-electrophile coupling of unactivated alkyl bromides with symmetrical tetrasulfides, forming unsymmetrical disulfide intermediates. This approach offers practicality and scalability for disulfide synthesis.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Shi-Yin Tian, Jing-Jing Ai, Jia-Hui Han, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: A photocatalytic synthesis method was developed to simultaneously construct two C-S/Se bonds and one C-C bond without the use of transition metals or other additives, using diphenyl disulfide or diphenyl diselenide as sulfur or selenium sources.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ying Chen, Fei Wang, Weidong Rao, Shusu Shen, Daopeng Sheng, Shun-Yi Wang
Summary: An efficient method for the copper-catalyzed ring-opening hydrolysis of silacyclobutanes to silanols was developed in this study. This strategy offers the advantages of friendly reaction conditions, simple operation, and good functional group compatibility. It also allows for the introduction of S-S bonds into organosilanol compounds in a single step. The successful gram scale synthesis demonstrates the potential of this protocol for practical industrial applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Letter
Chemistry, Organic
Yi-Fan Jiang, Wei-Chen Zhu, Xin-Yu Liu, Shi-Yin Tian, Jia-Hui Han, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: Here, a new method is provided to synthesize 1,3-dibenzenesulfonylpolysulfane (DBSPS), which reacts with boronic acids to produce thiosulfonates. Commercially available boron compounds significantly expand the range of thiosulfonates. Experimental and theoretical investigations reveal that DBSPS can generate both thiosulfone and dithiosulfone fragments, with the latter being unstable and decomposing into thiosulfonates.
Article
Chemistry, Organic
Wang Chen, Xin-yu Liu, Daopeng Sheng, Yi-Fan Jiang, Weidong Rao, Shu-Su Shen, Zhao-Ying Yang, Shun-Yi Wang
Summary: A nickel-catalyzed C-SS reductive cross-coupling reaction for producing unsymmetric disulfides has been developed. This approach exhibits a broad substrate scope, excellent functional group tolerance, and can be conducted under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Jia-Hui Han, Shi-Yin Tian, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: In this study, a visible-light-mediated selenylation/cyclization reaction using selenium radicals generated from diselenides as radical sources with acrylimide derivatives is described. This method provides a mild and effective approach for the synthesis of symmetrical selenosubstituted pyrrolidine-2,5-diones. The described catalytic strategy offers advantages such as mild reaction conditions, metal-free conditions, no additives required, easy operation, and a wide substrate range.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fei Wang, Ying Chen, Weidong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A Cu-catalyzed cascade reaction has been developed for the construction of S (Se)-containing organosilicon compounds using four-membered silacyclobutanes (SCBs) and thiosulfonates. The protocol exhibits a wide substrate scope, high functional group compatibility, and mild reaction conditions, enabling the formation of new C-S (Se) and Si-O bonds in a single step.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ying Chen, Daopeng Sheng, Fei Wang, Weidong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A Ni(II)/TPMPP-catalyzed reductive cross-coupling reaction has been reported for the synthesis of unsymmetric disulfides from benzyl oxalates and tetrasulfides. This method offers mild reaction conditions, wide substrate range, and easy operation, and has successfully achieved gram-scale synthesis of disulfides.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fei Wang, Ying Chen, Lutz Ackermann, Shun-Yi Wang
Summary: In this study, a selective cross-coupling reaction between unactivated alkyl bromides and diaryl tellurides was achieved using reductive nickel catalysis, leading to the synthesis of unsymmetrical alkyl-aryl tellurides with mild reaction conditions, high yields, easily accessible substrates, and a broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Bo-Xi Liu, Fei Wang, Ying Chen, Wei-Dong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A visible-light-promoted regioselective denitrogenative cross-coupling between benzotriazinones and selenosulfonates has been developed for the synthesis of ortho-selenylated benzamides. The reaction provides good yields and demonstrates a general substrate scope. Furthermore, this protocol has been successfully employed for the one-pot two-step synthesis of a series of ebselen and its analogs.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Lin Xu, Pei Xu, Yi-Ming Zhu, Weidong Rao, Shun-Yi Wang
Summary: This new method utilizes NaI/TBHP as catalyst to synthesize achiral axial 3,3'-biindole-2,2'-dibenzenesulfonothioate derivatives from arylsulfonyl hydrazides and indole-2-thiones under mild conditions without the need for a transition-metal catalyst.
ORGANIC CHEMISTRY FRONTIERS
(2021)