Article
Chemistry, Organic
Bijay Ketan Das, Tanumay Sarkar, Prabhat Kumar Maharana, Subhradeep Kar, Tharmalingam Punniyamurthy
Summary: In this study, stereospecific cascade C-N and C-O bonds formation of oxiranes with N-propargylamines was achieved using Zn/Ag relay catalysis, leading to the synthesis of functionalized dihydrooxazines. The reaction exhibited excellent tolerance towards various functional groups and was scalable for practical applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yunpeng Zhang, Daoyi Yang, Dengfu Lu, Yuefa Gong
Summary: A photoredox-enabled alkylative dearomatization of protected anilines is described. By using Ir catalyst and light irradiation, an N-carbamoyl-protected aniline and an alpha-bromo-carbonyl compound can be activated simultaneously, leading to the formation of a dearomatized cyclohexadienone imine as the main product through radical recombination. This method allows the preparation of a series of imines with contiguous quaternary carbon centers, which can be further converted into cyclohexadienones, cyclohexadienols, and cyclohexyl amines.
Article
Chemistry, Organic
Huaxin Zhang, Yongge Xiong, Jiang Bai, Ruchun Yang, Xian-Rong Song, Qiang Xiao
Summary: We introduce a highly efficient and practical method for synthesizing gem-dibromo 1,3-oxazines through 6-endo-dig cyclization of propargylic amides, using N-bromosuccinimide (NBS) as an electrophilic source. This metal-free reaction can be carried out under mild conditions, showing good compatibility with various functional groups and providing excellent yields of the desired products. Mechanistic studies indicate that the reaction proceeds through a double electrophilic attack of NBS on the propargylic amide substrate.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Physical
Amit Dahiya, Franziska Schoenebeck
Summary: This study unveils an efficient, mild, and modular arylation method of alkynylgermanes enabled by blue light-assisted gold catalysis, which has the potential to expand the modularity and scope in the construction of functional alkynes.
Article
Multidisciplinary Sciences
Lei Dai, Jiami Guo, Qingqin Huang, Yixin Lu
Summary: Alkynes are important and sustainable feedstocks used in industries such as pharmaceuticals, agrochemicals, and materials. However, efficient structural elaborations of alkynes, especially asymmetric multifunctionalization, have not been fully explored. Therefore, it is necessary to develop new asymmetric synthetic approaches to convert these chemical feedstocks into valuable chiral molecules.
Article
Chemistry, Multidisciplinary
James E. Baumann, Gojko Lalic
Summary: A new method for the differential dihydrofunctionalization of terminal alkynes has been developed, enabling the synthesis of allylic boronate esters through a reductive three-component coupling reaction. This transformation, promoted by a copper/palladium catalyst system, hydrofunctionalizes both pi-bonds of the alkyne. The method is compatible with a wide range of functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Nikolay V. V. Shcherbakov, Polina F. F. Kotikova, Elena I. I. Chikunova, Dmitry V. V. Dar'in, Vadim Yu. Kukushkin, Alexey Yu. Dubovtsev
Summary: The gold-catalyzed interplay between ynamides and aminocarbonyls provides a pathway to 2-aminoquinolines. This modular annulation reaction occurs under mild conditions and is compatible with various functionalities. Unlike other gold-catalyzed methods, this approach allows for the use of diverse aminocarbonyl substrates and allows for the variation of substituents in the 4th position of the quinoline. The obtained heterocyclic products demonstrate synthetic potential through post-modifications of the quinoline backbone and peripheral substituents.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Shu-Ming Kang, Shan-Shan Han, Yuan-Yuan Zhu, Zong-Quan Wu
Summary: A facile strategy to boost cooperative catalysis for alkyne hydration using polymer-supported catalysts was reported, with cobalt(III) porphyrin deliberately decorated onto stereoregular polyisocyanides to synthesize the functional polymer P1-Co. P1-Co exhibited high activity and good conversions, while irregular polymeric analogs and small-molecule controls performed poorly.
Article
Chemistry, Physical
Yang Gao, Simin Yang, Yanping Huo, Qian Chen, Xianwei Li, Xiao-Qiang Hu
Summary: A highly efficient NiH catalytic system was developed for the selective hydroamination of alkynes, leading to structurally diverse quinolines. This method is applicable to a wide range of alkynes and has shown utility in the functionalization of natural products and the synthesis of complex molecules. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and intramolecular cyclization of enamine intermediates.
Article
Chemistry, Multidisciplinary
Shashank P. Sancheti, Yukta Singh, Manoj V. Mane, Nitin T. Patil
Summary: This study reports the first gold-catalyzed 1,2-dicarbofunctionalization of alkynes using organohalides as non-prefunctionalized coupling partners. The mechanism of the reaction involves an oxidative addition/pi-activation pathway, which is different from the migratory insertion/cis-trans isomerization pathway observed in other transition metal catalysis. Mechanistic investigations including experiments, NMR studies, HR-MSMS analyses, and DFT calculations provide strong support for the proposed mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Abdusalom A. Suleymanov, Kay Severin
Summary: Recent developments have revealed that vinyl and alkynyl triazenes are highly interesting compounds with unique reactivity, enabled by the electron-donating properties of the triazenyl group. These compounds can be prepared in few steps from readily available starting materials, making them a promising area of study in synthetic organic and medicinal chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Li-Wen Zhan, Chuan-Jun Lu, Jia Feng, Ren-Rong Liu
Summary: This study reports for the first time that palladium compounds can catalyze the hydroarylation of 1-alkynylindoles with organoborons, resulting in the synthesis of chiral C-N atropisomers. The reaction conditions are mild and lead to excellent regio-, stereo- (Z-selectivity), and enantioselectivity. The simplicity, high stereoselectivity, and good functional group tolerance of this catalytic system make it highly attractive.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yang-Bo Chen, Li-Gao Liu, Can-Ming Chen, Yi-Xi Liu, Bo Zhou, Xin Lu, Zhou Xu, Long-Wu Ye
Summary: In this study, a copper-catalyzed atroposelective diyne cyclization was disclosed for the synthesis of a range of axially chiral arylpyrrole biaryls with good to excellent yields and enantioselectivities. This method represents the first synthesis of mono-substituted 3-arylpyrrole atropisomers and the first example of atroposelective diyne cyclization and atropisomer construction using vinyl cations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Lin-Jun Qi, Cui-Ting Li, Zheng-Qi Huang, Jia-Tian Jiang, Xin-Qi Zhu, Xin Lu, Long-Wu Ye
Summary: The study presents a novel copper-catalyzed asymmetric formal annulation reaction, which can synthesize a range of chiral oxygen-heterocycles via carbonyl ylides with excellent enantioselectivity and yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yanyan Zhang, Yunhong Han, Shengqing Zhu, Feng-Ling Qing, Xiao-Song Xue, Lingling Chu
Summary: This article describes a photochemically induced selective and divergent cyanation reaction of alkynes, enabled by phosphorus radicals. By using simple triarylphosphine as a co-catalyst, three cyanation reactions, including di-hydrocyanation, anti-Markovnikov hydrocyanation, and domino hydrocyanation/reduction, can be achieved, resulting in a wide array of alkyl dinitriles, alkenyl nitriles, and alkyl nitriles under mild conditions. Terminal and internal alkynes show high efficiency and excellent selectivity. Synthetic applications for biologically active agents and preliminary experimental and computational mechanistic studies are reported.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jesus Gonzalez, Alba de la Fuente, Maria J. Gonzalez, Laura Diez de Tejada, Luis A. Lopez, Ruben Vicente
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Kota Yamamoto, Enol Lopez, Pablo Barrio, Javier Borge, Luis A. Lopez
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Review
Chemistry, Multidisciplinary
Ruben Vicente
Summary: This review summarizes key reactivities relying on C-C bond cleavages of cyclopropenes, including both metal-catalyzed and metal-free transformations. The emphasis is on the synthetic utility and mechanistic aspects of various methodologies discussed, covering a range of reactions involving vinyl carbenes, metathesis processes, heterocycles syntheses, SEAr reactions, metalation-ring opening sequences, and cycloadditions. The focus is on results from 2007 to 2019, with relevant pioneering transformations eventually included.
Article
Chemistry, Organic
Olaya Bernardo, Kota Yamamoto, Israel Fernandez, Luis A. Lopez
Summary: This study reports the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, common structural motifs in bioactive compounds. The reaction proceeds with complete regio- and stereoselectivity, with the silyl group serving as a regio- and stereocontrolling element. Additionally, the use of alkynylsilanes as reaction partners yielded skipped enynes through C(sp)-C(sp(3)) coupling.
Article
Chemistry, Multidisciplinary
Olaya Bernardo, Silvia Gonzalez-Pelayo, Israel Fernandez, Luis A. Lopez
Summary: The gold-catalyzed reaction of propargyl esters with alkynylsilanes produces vinylallene derivatives through consecutive [1,2]-acyloxy/[1,2]-silyl rearrangements. This transformation features good yields, full atom-economy, a broad substrate scope, easy scale-up, and low catalyst loadings. The reaction mechanism involves the generation of a gold vinylcarbene intermediate and a type II-Dyotropic rearrangement involving the silyl group and the metal fragment.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
[Anonymous]
Summary: This article reviews the recent advances in the synthesis and applications of ferrocene-fused nitrogen heterocycles. The transfer of powerful transition-metal-catalyzed methodologies for C-H bond functionalization of benzene derivatives to ferrocene has played a significant role in this field.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Review
Chemistry, Inorganic & Nuclear
Olaya Bernardo, Silvia Gonzalez-Pelayo, Luis A. Lopez
Summary: The marriage of heterocyclic compounds with ferrocene has been a fruitful field of research, with several ferrocene-embedded heterocyclic compounds reported in recent years. The synergistic combination of properties from both heterocyclic and metallacyclic motifs in fused systems has led to interesting applications, particularly in asymmetric catalysis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Review
Chemistry, Medicinal
Alba Fombona-Pascual, Javier Fombona, Ruben Vicente
Summary: This research analyzes the development and potential of augmented reality technology in the field of chemistry for three-dimensional molecule visualization. The study finds that there are already some successful examples of augmented reality applications in education and research environments, although traditional two-dimensional screen visualization is still more commonly used for teaching.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2022)
Article
Chemistry, Organic
Olaya Bernardo, Javier Gonzalez, Javier Borge, Luis A. Lopez
Summary: In this study, we successfully reported a regioselective synthesis method for silyl-substituted cyclopentadienyl esters through gold-catalyzed migratory cycloisomerization of silyl-substituted vinylallenes. Additionally, we have identified more straightforward synthesis conditions using the multifaceted nature of the gold catalyst, by reacting propargyl esters and alkynylsilanes.
Article
Chemistry, Applied
Patricia Garcia-Martinez, Olaya Bernardo, Javier Borge, Javier Gonzalez, Luis A. Lopez
Summary: The BF3 & sdot;OEt2-catalyzed reaction of azulene with N-protected aziridines provides a general and efficient method for synthesizing phenethylamine-azulene conjugates with high regioselectivity (up to 91% yield). Stereochemical studies and DFT calculations confirm a concerted SN2-type mechanism for the ring-opening reaction of aziridine.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Dario Coto, Iratxe Barbolla, Ruben Vicente
Summary: Silylcyclopropenes as precursors of alpha-silyl vinyl carbenes can undergo reactions with alkenes, leading to the synthesis of cyclopropylsilanes and cis-1,2-disubstituted cyclopropanes with high selectivity.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Ruben Vicente, Eva Tudela, Miguel A. Rodriguez, Angel L. Suarez-Sobrino, Alfredo Ballesteros
Summary: The synthesis of specific cyclopropane-tethered 1,5-enynes, known as 6-alkynyl-4-alkylidenebicyclo[3.1.0]hex-2-enes, led to the discovery of an unprecedented gold-catalyzed rearrangement to indenes. A computational study of the mechanism behind this significant skeleton rearrangement is also presented.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Inorganic & Nuclear
Nicola Panza, Giorgio Tseberlidis, Alessandro Caselli, Ruben Vicente
Summary: This article presents an overview of the recent developments in pyridine-containing 12-membered tetraazamacrocycles with pyclen or Py2N2 backbones and their metal complexes from 2017 to the present. It includes the syntheses of newly described ligands and complexes relevant to medicine, as well as the reactivity of complexes bearing these ligands and their applications in catalysis.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Luis A. Lopez, Javier Gonzalez
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
