Article
Chemistry, Physical
Qiao Ren, Tingting Cao, Chunnian He, Meihua Yang, Haitao Liu, Lei Wang
Summary: The highly atroposelective construction of axially chiral N-arylindolocarbazoles via Rh(II)-catalyzed intermolecular carbene N-H insertion reactions provides a rapid access to enantio-enriched products with moderate to good yields and high enantioselectivities. The synthetic utility of this method is emphasized by late-stage functionalization of representative natural products and bioactive molecules, as well as polyaromatic ring construction and chiral phosphoric acid synthesis from N-arylindolocarbazoles, highlighting its practical value in materials chemistry and catalytic asymmetric synthesis.
Article
Chemistry, Organic
Peng Guo, Jun-Fa Han, Guo-Cai Yuan, Lin Chen, Jia-Bin Liao, Ke-Yin Ye
Summary: A cobalt-catalyzed aminofluorination reaction of styrenes with N-fluorosulfonamides has been developed, with the selectivity easily switched to diamination by the addition of PPh3. Both transformations are tolerant to a wide array of substrates under mild reaction conditions.
Article
Chemistry, Multidisciplinary
Quanxin Peng, Meirong Huang, Guangyang Xu, Yan Zhu, Ying Shao, Shengbiao Tang, Xinhao Zhang, Jiangtao Sun
Summary: An intermolecular enantioselective N-alkylation reaction of 1H-indoles has been developed using a cooperative rhodium and chiral phosphoric acid catalyzed N-H bond insertion reaction. The reaction produces N-alkyl indoles with high yields and excellent enantioselectivities, even with both alpha-aryl and alpha-alkyl diazoacetates. This method requires only a small amount of rhodium catalyst and chiral phosphoric acid, and computational studies provide insights into the mechanism and selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Dharmendra Kumar, Malleswara Rao Kuram
Summary: Easy access to divergent products through chemoselective copper-catalyzed carbene insertion onto N-H bonds of tryptamine derivatives is achieved by varying the nucleophilicity of the aliphatic NH and electron-donating or electron-withdrawing groups. The reaction provides N-H insertion products with broad substrate scope and good yields.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Bo Li, Cheng-Wei Ju, Wenlong Wang, Yanwei Gu, Shuai Chen, Yongrui Luo, Haozhe Zhang, Juan Yang, Hai-wei Liang, Mischa Bonn, Klaus Mu''llen, William A. Goddard, Yazhou Zhou
Summary: The study reports a heterogeneous single-atom Pt-catalyzed Heck reaction, the first of its kind on SACs, using a supercritical carbon-dioxide-assisted protocol. The research showcases how SACs can introduce underexplored coordination structures, offering potential for transferring migratory-insertion-based reactions to heterogeneous SACs.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Multidisciplinary
Benjamin D. Bergstrom, Leslie A. Nickerson, Jared T. Shaw, Lucas W. Souza
Summary: Donor/donor and donor carbenes, although relatively new in carbene chemistry, have shown exquisite chemo- and stereo-selectivity in various insertion reactions. Recent studies have demonstrated high levels of diastereo- and enantioselectivity with different transition metal catalysts. Methods involving diazo-based carbene precursors and diazo-free metal carbenes have both been successful, providing context for future developments in this emerging field.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Rongxiang Chen, Guoyang Ma, Yawen Li, Jinju Zhang, Ran Xia, Kai-Kai Wang, Lantao Liu
Summary: This study describes a mild, convenient, and effective strategy using TBAI as a catalyst to catalyze the S-H and N-H insertion reactions of alpha-diazoesters with thiophenols and aromatic amines under metal-free conditions, providing a synthetic route for various thioethers and 2-amino-2-oxoacetates in moderate to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Wei Yang, Maoping Pu, Xiaobin Lin, Min Chen, Yanji Song, Xiaohua Liu, Yun-Dong Wu, Xiaoming Feng
Summary: In this study, a novel method was developed for the synthesis of vinyl gamma-amino amides with high gamma-selectivity and enantioselectivity using a high-spin chiral complex catalyst. The calculation showed a spin state change from quartet cobalt(II) complex to doublet Co(II)-carbene species for Z-selective and enantioselective nucleophilic addition.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Xiaofeng Liu, Ying Shao, Jiangtao Sun
Summary: A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, providing N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to this unprecedented reaction is the use of CpRu(PPh3)(2)Cl as the catalyst and sulfoxonium ylides as the alkylation reagents, which can also be applied to 7-azaindoles with slight variations in reaction conditions. Furthermore, sulfonium ylides are also suitable alkylation reagents for good selectivity in N-alkylation of 2-pyridones.
Article
Chemistry, Physical
Satabdi Bera, Saikat Roy, Shyam Chand Pal, Anakuthil Anoop, Rajarshi Samanta
Summary: This study demonstrates an efficient Ir(III)-catalyzed straightforward intermolecular N-arylation of acyclic aliphatic amides using quinone diazide as a coupling partner. The reaction conditions are simple and mild with a broad substrate scope, and the bidentate picolinamide group is essential for successful transformation. Mechanistic studies and DFT calculations highlight a migratory insertion-based pathway. The developed method exhibits different reactivities compared to reactions using related diazo/azide congeners under Rh(III)/Ir(III) catalysis.
Article
Multidisciplinary Sciences
Zhaohong Liu, Hongwei Wang, Paramasivam Sivaguru, Steven P. Nolan, Qingmin Song, Weijie Yu, Xinyu Jiang, Edward A. Anderson, Xihe Bi
Summary: The authors present a silver-catalyzed method for C-H benzylation of ethers, using a more common and stable starting material compared to traditional methods. This approach allows for the efficient synthesis of medicinally relevant ether compounds.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Zilong Huang, Jie Lin, Juan Ma, Liandi Wang, Yong-Gui Zhou, Zhengkun Yu
Summary: Carbene insertion into C(sp(2))-H bonds of internal alkenes was achieved in air using HFIP as both the mediator and solvent, along with borane B(C6F5)(3) as the catalyst. The reaction showed high yields (47-84%) and broad substituent tolerance, providing an efficient route to synthesize 3-vinylated oxindole and indole derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Jake R. Jagannathan, Karina Targos, Annaliese K. Franz
Summary: Carbene insertion into Si-H bonds of polyhedral oligomeric silsesquioxanes (POSS) using dirhodium(II) carboxylates as catalysts allows for the synthesis of highly functionalized siloxane nanomaterials. This method results in the production of 20 new POSS compounds with diverse structures, containing both ester and aryl groups for further derivatization. The transformations of aryl(ester)-functionalized POSS compounds, including ester hydrolysis and Suzuki-Miyaura cross-coupling, demonstrate the versatility and potential applications of these highly functionalized substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Tzu-Lun Liu, Meng-Li Jhou, Cheng-En Hsieh, Chia-Jung Lin, Hsiu-Hui Su, Chih-Ming Chou
Summary: This study presents a protocol for the preparation of functionalized N-allyl-N-aryl sulfonamides via palladium-catalyzed intramolecular decarboxylative N-allylation reaction, showing good regioselectivity. Additionally, transformation of N-allyl-N-aryl sulfonamide into 4-aryl-1,2,3,4-tetrahydroquinoline and nitrogen-containing beta-hydroxysulfide bioactives has been demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yong Wu, Yongquan Ning, Xinyue Han, Peiqiu Liao, Ying Xia, Paramasivam Sivaguru, Xihe Bi
Summary: The silver-catalyzed formal insertion of a vinylcarbene into unstrained C(CO)-C bonds of 1,3-diketones using vinyl-N-triftosylhydrazones as precursors allows for the rapid synthesis of 2-vinyl-substituted 1,4-diketones with good functional group tolerance and substrate scope. Preliminary theoretical calculations suggest that the reaction proceeds through a stepwise enol cyclopropanation/retro-aldol pathway.
Article
Chemistry, Physical
Antonio Tinoco, Yang Wei, John-Paul Bacik, Daniela M. Carminati, Eric J. Moore, Nozomi Ando, Yong Zhang, Rudi Fasan
Article
Chemistry, Multidisciplinary
David A. Vargas, Rahul L. Khade, Yong Zhang, Rudi Fasan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Physical
Rahul L. Khade, Ajay L. Chandgude, Rudi Fasan, Yong Zhang
Article
Chemistry, Organic
Viktoria Steck, Gopeekrishnan Sreenilayam, Rudi Fasan
Article
Chemistry, Physical
Daniela M. Carminati, Rudi Fasa
Article
Chemistry, Physical
Rudi Fasan, S. B. Jennifer Kan, Huimin Zhao
Article
Oncology
Pierre-Antoine Bissey, Pauline Mathot, Catherine Guix, Melissa Jasmin, Isabelle Goddard, Clelia Costechareyre, Nicolas Gadot, Jean-Guy Delcros, Sachitanand M. Mali, Rudi Fasan, Andre-Patrick Arrigo, Robert Dante, Gabriel Ichim, Patrick Mehlen, Joanna Fombonne
Article
Chemistry, Physical
Xinkun Ren, Ajay L. Chandgude, Rudi Fasan
Article
Chemistry, Multidisciplinary
Andrew E. Owens, Jacob A. Iannuzzelli, Yu Gu, Rudi Fasan
ACS CENTRAL SCIENCE
(2020)
Article
Biochemistry & Molecular Biology
Maria Agustina Vila, Viktoria Steck, Sonia Rodriguez Giordano, Ignacio Carrera, Rudi Fasan
Article
Chemistry, Multidisciplinary
Viktoria Steck, Joshua N. Kolev, Xinkun Ren, Rudi Fasan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Editorial Material
Chemistry, Physical
Xinkun Ren, Rudi Fasan
Article
Biochemistry & Molecular Biology
Alfons J. Pineda-Knauseder, David A. Vargas, Rudi Fasan
BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Sai Shashank Chavali, Sachitanand M. Mali, Jermaine L. Jenkins, Rudi Fasan, Joseph E. Wedekind
JOURNAL OF BIOLOGICAL CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Jacob A. Iannuzzelli, Rudi Fasan
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)