Article
Chemistry, Multidisciplinary
Xu Ma, Yongliang Zhang, Xijun Zhu, Liming Zhang
Summary: A solution to the synthetically challenging stereoselective construction of 1,2-cis furanosidic linkage has been developed based on gold catalysis and the deployment of the directing-group-on-leaving-group strategy. The reactions exhibit good to excellent selectivities and high yields, with most being completed in a short period of time. A wide range of 1,2-cis-furanosides have been prepared, offering new opportunities for research in medicine and materials.
Article
Chemistry, Multidisciplinary
Hengfu Xu, Richard N. Schaugaard, Jiayi Li, H. Bernhard Schlegel, Hien M. Nguyen
Summary: This study reports a new stereoselective method for the formation of the 1,2-cis furanosidic linkage using phenanthroline catalysts. The method operates under mild conditions and provides good yields and high selectivities for biologically relevant oligosaccharides and polysaccharides. NMR experiments and density functional theory calculations support an associative mechanism, and the reaction is applicable to various furanosyl bromide donors.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Xiaolei Li, Jicheng Wu, Weiping Tang
Summary: Human glycans are mainly composed of nine common sugar building blocks, while hundreds of different monosaccharides have been found in bacteria. A new efficient strategy has been developed to access rare sugars from common monosaccharides, which can be used for constructing glycoside skeletons in natural products or bioactive compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Qing-Yun Fang, Jie Han, Mingzhe Qin, Weipeng Li, Chengjian Zhu, Jin Xie
Summary: Reported here is a three-component 1,2-difunctionalization reaction of alkenes, unactivated alkyl bromides, and nucleophiles (e.g., amines and indoles) using a trinuclear gold catalyst [Au-3(tppm)(2)](OTf)(3). This reaction enables facile 1,2-aminoalkylation and 1,2-alkylarylation and exhibits a broad reaction scope and excellent functional group compatibility (>100 examples with up to 96% yield). It also provides a robust formal [2+2+1] cyclization strategy for the concise construction of pyrrolidine skeletons under mild reaction conditions. Mechanistic studies support an inner-sphere single electron transfer pathway for the successful cleavage of inert C-Br bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Seema Panicker, Aristides Marcano, Shehu Isah, Brianna Kenney, Bizuneh Workie, Changseok Han, Haesung Lee, Mohamed M. Chehimi, Ahmed A. Mohamed
Summary: The synthesis of tetrazonium gold(III) salts with two different geometries was studied, using AuNPs constructed with a mild reducing agent as the main material. It was found that the cis-AuNPs were smaller than the trans-AuNPs, and the presence of metallic gold in both isomers was confirmed through various analytical methods.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Artur Mardyukov, Raffael C. Wende, Peter R. Schreiner
Summary: 1,2-Ethenediols are key intermediates in prebiotic and interstellar syntheses of carbohydrates. In this study, we synthesized these enediols in the gas phase and trapped them in cryogenic argon matrices. Importantly, when subjected to photolysis at a wavelength of 180-254 nm, the enols rearrange into the simplest sugar, glycolaldehyde.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Anastasia Louka, Manolis Stratakis
Summary: The study demonstrates that terminal alkynes react with unactivated digermane to form cis-1,2-digermylated alkenes under the catalysis of Au/TiO2; it also achieves the hydrogermylation of terminal allenes with a highly regioselective mode forming vinylgermanes on the more substituted double bond. Moreover, preliminary results are shown for the Pd nanoparticle-catalyzed C-C coupling of 1,2-digermyl alkenes with aryl iodides.
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)
Article
Chemistry, Multidisciplinary
Xin Liu, Lukman O. Alimi, Niveen M. Khashab
Summary: An intrinsically porous triazene macrocycle is reported to selectively separate cis-1,2-dichloroethene from a mixture of cis- and trans-DCE with a purity of over 96% through enhanced host/guest C-H...pi intermolecular interactions. The macrocycle can be reused multiple times without any decrease in performance, supporting the sustainability of using molecular sieves in chemical separation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Neyen Romano, Nicholas M. Hein, Kevin Basemann, Youngran Seo, Michel R. Gagne
Summary: This study reports the use of a bis-oxazoline Cu2+ catalyst for the selective azidation of sugars. Experimental and computational results suggest that the catalyst activates azide through a silylium transfer mechanism, leading to the azidation of sugars.
Article
Chemistry, Organic
Yingle Feng, Tiantian Guo, Han Yang, Guoqiang Liu, Qi Zhang, Shengyong Zhang, Yonghai Chai
Summary: A transition-metal-catalyzed O-alkylation method was developed for the regio- and stereoselective construction of 1,2-cis-glycosidic linkages. Using nonprecious and readily available Ni(II) as a catalyst, 1,2-cis-glycosides were obtained via O-alkylation of 1,2-carbohydrate diols without the need for protecting groups or anomeric leaving groups.
Article
Chemistry, Applied
Robin Heckershoff, Lukas Eberle, Garrett May, Petra Kraemer, Frank Rominger, Matthias Rudolph, A. Stephen K. Hashmi
Summary: The recently developed gold-catalyzed synthesis of indolo[1,2-a]quinolines has been successfully expanded to bidirectional approaches, allowing access to two heptacyclic structural motifs. New nitrogen-containing heptacycles, benzobispyrrolo[1,2-a]quinolines, were synthesized using alkynylated benzodipyrrole derivatives. The study revealed important structure-effect relationships between solid-state structures and photophysical properties.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Junggil Kim, Sang Kyu Kim
Summary: The photofragmentation dynamics of the cis and trans isomers of 1,2-dibromoethylene were studied using multiphoton excitation, revealing isomer-specific reactivity. The Br-2(+) product ion from the cis isomer preferentially originates from a specific photon energy for unimolecular reactions, while anisotropic kinetic energy components of Br+ and Br-2(+) from the trans isomer appear at higher photon energies. The transition dipole moment of the strongest oscillator strength indicates the orientation of the transition for the trans and cis isomers, leading to fast anisotropic components in the product distributions.
JOURNAL OF CHEMICAL PHYSICS
(2021)
Article
Chemistry, Multidisciplinary
Sagar R. Mudshinge, Yuhao Yang, Bo Xu, Gerald B. Hammond, Zhichao Lu
Summary: The first C-SCF3/SeCF3 cross-coupling reactions using gold redox catalysis are reported. The new method enables the one-stop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers, with a broad substrate scope. It is scalable and can be applied to late-stage functionalization of bioactive molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Akash G. Tathe, Urvashi, Amit K. Yadav, Chetan C. Chintawar, Nitin T. Patil
Summary: The study reported a gold-catalyzed 1,2-aminoarylation of alkenes using external amines as coupling partners. By carefully optimizing the reaction conditions, the researchers were able to achieve highly chemoselective access to the desired aminoarylation products by controlling the concentration of base. This strategy provided straightforward access to medicinally relevant derivatives like 3-aminochroman, 2-aminotetrahydronaphthalene, and 2-aminoindane.
Article
Biochemistry & Molecular Biology
Shivaji A. Thadke, Mahesh Neralkar, Srinivas Hotha
CARBOHYDRATE RESEARCH
(2016)
Article
Multidisciplinary Sciences
Shivaji A. Thadke, Bijoyananda Mishra, Maidul Islam, Sandip Pasari, Sujit Manmode, Boddu Venkateswara Rao, Mahesh Neralkar, Ganesh P. Shinde, Gulab Walke, Srinivas Hotha
NATURE COMMUNICATIONS
(2017)
Article
Biochemistry & Molecular Biology
Shivaji A. Thadke, J. Dinithi R. Perera, V. M. Hridya, Kirti Bhatt, Ashif Y. Shaikh, Wei-Che Hsieh, Mengshen Chen, Chakicherla Gayathri, Roberto R. Gil, Gordon S. Rule, Arnab Mulcherjee, Charles A. Thornton, Danith H. Ly
Article
Biochemistry & Molecular Biology
Wei-Che Hsieh, Raman Bahal, Shivaji A. Thadke, Kirti Bhatt, Krzysztof Sobczak, Charles Thornton, Danith H. Ly
Article
Biochemistry & Molecular Biology
Raman Bahal, Arunava Manna, Wei-Che Hsieh, Shivaji A. Thadke, Gopalsamy Sureshkumar, Danith H. Ly
Article
Biochemistry & Molecular Biology
Shivaji A. Thadke, Mritunjoy Kar, Sayam Sen Gupta, Srinivas Hotha
CARBOHYDRATE RESEARCH
(2011)
Article
Biochemistry & Molecular Biology
Srinivasa Rao Vidadala, Shivaji A. Thadke, Srinivas Hotha, Sudhir Kashyap
JOURNAL OF CARBOHYDRATE CHEMISTRY
(2012)
Article
Chemistry, Organic
Srinivasa Rao Vidadala, Shivaji A. Thadke, Srinivas Hotha
JOURNAL OF ORGANIC CHEMISTRY
(2009)
Article
Chemistry, Organic
Shivaji A. Thadke, Srinivas Hotha
ORGANIC & BIOMOLECULAR CHEMISTRY
(2014)
Article
Chemistry, Organic
Shivaji A. Thadke, Bijoyananda Mishra, Srinivas Hotha
Article
Chemistry, Organic
Shivaji A. Thadke, Srinivas Hotha
TETRAHEDRON LETTERS
(2010)
Article
Chemistry, Organic
Wei-Che Hsieh, Ashif Y. Shaikh, J. Dinithi R. Perera, Shivaji A. Thadke, Danith H. Ly
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Isha Dhami, Shivaji A. Thadke, Danith H. Ly
Summary: Gamma peptide nucleic acids (PNAs) are nucleic acid mimics that can bind to DNA or RNA with high affinity and sequence specificity. Researchers have developed a universal monomer system that allows for rapid and selective chemical modification and diversification, expanding the applications of gamma PNAs.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shivaji A. Thadke, V. M. Hridya, J. Dinithi R. Perera, Roberto R. Gil, Arnab Mukherjee, Danith H. Ly
COMMUNICATIONS CHEMISTRY
(2018)