Article
Chemistry, Applied
Heng-Tong Qu, Zeng-Hui Wu, Guo-Chen Zhong, Yan-Chun Zhang, Cheng-Tao Feng, Kun Xu
Summary: An aerobic Mn(III)-catalyzed one-pot three-component synthesis of 5-cyano-pyrazolo[1,5-a]pyrimidines has been developed, which relies on the synergistic combination of Strecker reaction and oxidatively-induced 6 pi-azacyclization. This protocol offers a step-economic, regioselective, and functionally tolerant strategy to obtain 5-cyano-pyrazolo[1,5-a]pyrimidines, distinct from previous reports using toxic cyanating agents or multistep synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Xiang Sun, Tobias Ritter
Summary: In this study, a novel method for polyfluoroarylation of aliphatic carboxylic acids was reported, with broad substrate scope and high functional group tolerance. Small complex molecules such as natural products and drugs can be modified through late-stage modification.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Shi-Hui He, Guang-Le Chen, Xing-Yu Gong, Gui-Zhen Ao, Feng Liu
Summary: In this study, a redox-neutral and mild approach for radical sulfinylation of redox-active esters via dual photoredox and copper catalysis was developed, leading to a series of functionalized sulfoxides. The reaction demonstrated broad substrate scope and high compatibility with various functional groups. The practicality, scalability, and potential for late-stage modification of bioactive pharmaceuticals make this chemistry highly valuable.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Alberto F. Garrido-Castro, Yuta Hioki, Yoshifumi Kusumoto, Kyohei Hayashi, Jeremy Griffin, Kaid C. Harper, Yu Kawamata, Phil S. Baran
Summary: This study presents a metal-free electrochemical decarboxylation method for the synthesis of olefins from alkyl carboxylic acids, providing a simpler and alternative approach for olefin synthesis. The method maintains the quality of the electrode surface and local pH through alternating polarity, allowing for chemoselective reactions on conventionally difficult substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Fachao Yan, Zijun Huang, Chen-Xia Du, Jian-Fei Bai, Yuehui Li
Summary: The FeI2-catalyzed reductive Strecker type reaction of formamides was reported, which successfully produced amino acetonitriles instead of aldehydes with higher yields than Ir or Rh catalysts. This method demonstrated the ability to one-pot construct complex molecules and conveniently produce homologated carboxylic acids from aldehydes.
JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Eloy P. Gomez-Oliveira, Daniel Reinares-Fisac, Lina M. Aguirre-Diaz, Fatima Esteban-Betegon, Mercedes Pintado-Sierra, Enrique Gutierrez-Puebla, Marta Iglesias, M. Angeles Monge, Felipe Gandara
Summary: This study synthesized and characterized three new bismuth metal-organic frameworks (MOFs), and demonstrated their catalytic activity in the one-pot multicomponent Strecker reaction. Among the MOFs, BiPF-7 exhibited high stability and catalytic activity, and the interaction between catalytic substrates and metal centers was analyzed through crystallography.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Kai Yang, Yukang Wang, Sanzhong Luo, Niankai Fu
Summary: In this study, we developed an electrophotochemical metal-catalyzed protocol for direct asymmetric decarboxylative cyanation of aliphatic carboxylic acids. By utilizing the synergistic merging of electrophotochemical cerium catalysis and asymmetric electrochemical copper catalysis, mild reaction conditions were achieved for the formation and utilization of carbon-centered radicals. This environmentally benign method smoothly converts a diverse array of arylacetic acids into the corresponding alkyl nitriles in good yields and enantioselectivities without using chemical oxidants or pre-functionalization of the acid substrates and can be readily scaled up.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Susana Herrera, Kennett Rivero, Alexis Guzman, Jonathan Cedeno, Jaroslava Miksovska, Raphael G. Raptis
Summary: This study synthesized a new family of mononuclear indium complexes, trianionic hexanuclear indium complexes, and multicolour emitting polymeric complexes. The complexes were characterized using crystallography and NMR techniques. The study found that these complexes exhibit fluxional behavior and identified the causes of this behavior.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Physical
Huanhuan Li, Sabry H. H. Younes, Shaohang Chen, Peigao Duan, Chengsen Cui, Ron Wever, Wuyuan Zhang, Frank Hollmann
Summary: In this study, we report the chemoenzymatic bromodecarboxylation (Hunsdiecker-type) of alpha,ss-unsaturated carboxylic acids using a highly stable chloroperoxidase. The generated hypobromite from H2O2 and bromide reacts spontaneously with a broad range of unsaturated carboxylic acids, yielding the corresponding vinyl bromide products. Selectivity issues, caused by the undesired addition of water to the intermediate bromonium ion, were effectively solved by manipulating the reaction medium. The obtained vinyl bromides can serve as versatile starting materials for various cross-coupling and pericyclic reactions.
Review
Chemistry, Multidisciplinary
Andrii Varenikov, Evgeny Shapiro, Mark Gandelman
Summary: Decarboxylative halogenation is a crucial method for synthesizing organic halides by converting carboxylic acids to the corresponding organic halides. This method involves the synthesis of organic iodides, bromides, chlorides, and fluorides, providing a wide range of methods and advantages.
Article
Chemistry, Multidisciplinary
Xiangli Yi, Runze Mao, Lara Lavrencic, Xile Hu
Summary: The study presents a decarboxylative coupling reaction using photoredox and copper catalysis to convert alkyl carboxylic acids into polyfluoroaryl compounds. The method demonstrates broad scope and good functional group compatibility, with the potential to achieve a wide range of F-substitution patterns on the aryl groups. Mechanistic study suggests a [Cu-(Ar-F)(2)] species may be responsible for the transfer of polyfluoroaryl groups to alkyl radicals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Romane Troadec, Sofia Nestora, Celine Niquet-Leridon, David Marier, Philippe Jacolot, Elodie Sarron, Stephanie Regnault, Pauline M. Anton, Celine Jouquand
Summary: This study aimed to assess the impact of using sourdough or yeast as a leavening agent for French bread making on the Maillard reaction and the bifidogenic effect. The findings indicated that the levels of Maillard reaction precursors varied depending on the leavening agent used, resulting in different Maillard reactions during baking. The sourdough bread showed a higher bifidogenic effect compared to yeast bread.
Article
Biochemistry & Molecular Biology
Seyed Ali Mousavi-Mashhadi, Ali Shiri
Summary: This work introduces a green and cost-effective method for the synthesis of alpha-amino nitriles using halloysite as a natural catalyst. The chemical and physical structure of halloysite was thoroughly characterized, and the reaction conditions were optimized to achieve good yields. The study also revealed the influence of substituent electron properties on the efficiency of the reaction, and demonstrated the recyclability of the catalyst.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Inorganic & Nuclear
Yansong Jiang, Jing Sun, Xiaona Yang, Jieyu Shen, Yu Fu, Yong Fan, Jianing Xu, Li Wang
Summary: The synthesis of a new 3D cadmium metal-organic framework with good solvent tolerance and catalytic activity for organic transformation reactions was achieved in this study. Integrating this framework with PVDF polymer led to the successful preparation of mixed-matrix membranes with excellent dispersion of Lewis acid catalytic sites and recyclability. The Cd-based MOF and MMMs show promising potential for producing benzimidazole and amino acid derivatives with good catalytic activity and recyclability.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
M. Angelica M. Rocha, Manuel A. Coimbra, Silvia M. Rocha, Claudia Nunes
Summary: The use of chitosan-genipin films as a technological adjuvant for white wine preservation offers new opportunities for winemaking industries, replacing sulfur dioxide while maintaining the varietal key odorants and organoleptic characteristics. The study shows that the contact of these films with white and red wines can retain long carbon chain volatile compounds and promote the formation of compounds that enhance the wines aroma, maintaining their varietal notes.
APPLIED SCIENCES-BASEL
(2021)
Article
Chemistry, Multidisciplinary
Anirudra Paul, Jae Hyun Kim, Scott D. Daniel, Daniel Seidel
Summary: Despite efforts by practitioners, direct alpha-C-H bond functionalization of unprotected alicyclic amines is rare. A new method utilizing N-lithiated alicyclic amines has been developed, providing a convenient approach to achieve functionalization reactions under mild conditions. This method offers a new pathway for the synthesis of beta-amino ketones with regioselective alpha'-alkylation, and potential for one-pot synthesis of polycyclic dihydroquinolones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Jae Hyun Kim, Anirudra Paul, Ion Ghiviriga, Daniel Seidel
Summary: Enolizable cyclic imines obtained in situ from lithium amides by oxidation with simple ketone oxidants can be readily alkylated with a range of enolates to provide mono- and polycyclic beta-aminoketones in a single operation, including the natural product (+/-)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations promoted by BF3 etherate. Moreover, beta-aminoesters derived from ester enolates can be converted to the corresponding beta-lactams.
Article
Chemistry, Medicinal
Stephanie L. Slania, Deepankar Das, Ala Lisok, Yong Du, Zirui Jiang, Ronnie C. Mease, Steven P. Rowe, Sridhar Nimmagadda, Xing Yang, Martin G. Pomper
Summary: Two new small molecules, QCP01 and [In-111]QCP02, based on (4-quinolinoyl)-glycyl-2-cyanopyrrolidine were synthesized and characterized for imaging of fibroblast activation protein (FAP). Both molecules demonstrated nanomolar inhibition of FAP and selective binding to FAP-expressing tumors in vivo. [In-111]QCP02 showed high uptake in FAP-positive tumors, indicating its potential as an imaging agent for FAP-targeted therapy.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Weijie Chen, Daniel Seidel
Summary: Polycyclic lactams are prepared in a single operation from otoluamides and cyclic amines, utilizing transient cyclic imines generated in situ from lithium amides and simple ketone oxidants. The annulation process involves imines like 1-pyrroline and 1-piperideine engaging lithiated o-toluamides, with undesired side reactions suppressed through careful selection of reaction conditions.
Article
Chemistry, Organic
Daniel A. Valles, Subhradeep Dutta, Anirudra Paul, Khalil A. Abboud, Ion Ghiviriga, Daniel Seidel
Summary: This one-pot procedure allows for the sequential, regioselective, and diastereoselective introduction of the same or two different substituents to the alpha- and alpha'-positions of unprotected azacycles using corresponding organolithium compounds. Various azacycles like pyrrolidines, piperidines, azepanes, and piperazines are included in the scope of this transformation.
Review
Chemistry, Organic
Weijie Chen, Daniel Seidel
Summary: This review provides a comprehensive overview of condensation-based methods for C-H bond functionalization of amines using azomethine ylides as key intermediates, which allow rapid transformation of simple starting materials into complex amines.
SYNTHESIS-STUTTGART
(2021)
Article
Multidisciplinary Sciences
O. C. Rogers, D. M. Rosen, L. Antony, H. M. Harper, D. Das, X. Yang, I Minn, R. C. Mease, M. G. Pomper, S. R. Denmeade
Summary: Prostate cancer cells have low proliferative rate and high levels of prostate-specific proteases. Utilizing PSMA inhibitors conjugated with toxins can selectively kill prostate cancer cells, demonstrating selective toxicity in vitro.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Organic
Subhradeep Dutta, Bowen Li, Dillon R. L. Rickertsen, Daniel A. Valles, Daniel Seidel
Summary: This review provides a concise overview of the methods that enable the functionalization of sp(3) C-H bonds in amines and their derivatives.
Article
Chemistry, Organic
Anirudra Paul, Camille Vasseur, Scott D. Daniel, Daniel Seidel
Summary: Relatively unstable cyclic imines, generated from alicyclic amines via oxidation of their lithium amides with simple ketone oxidants, react with aryllithium compounds containing a leaving group on an ortho-methylene functionality to form polycyclic isoindolines in a single step. The transformation can be applied to pyrrolidine, piperidine, azepane, azocane, and piperazine.
Article
Radiology, Nuclear Medicine & Medical Imaging
Catherine A. Foss, Alvaro A. Ordonez, Ravi Naik, Deepankar Das, Andrew Hall, Yunkou Wu, Robert F. Dannals, Sanjay K. Jain, Martin G. Pomper, Andrew G. Horti
Summary: The study presents the radiosynthesis of JNJ-28312141 and its specific binding to CSF1R+ macrophages, delineating granulomatous lesions in a murine model of pulmonary TB using PET.
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING
(2022)
Article
Chemistry, Multidisciplinary
Alafate Adili, Angie B. Korpusik, Daniel Seidel, Brent S. Sumerlin
Summary: Visible light-mediated direct decarboxylation is a versatile technique for the synthesis of functional materials with tailored compositions and properties. This process allows for the generation of carbon-centered radicals in polymer chains without the need for preactivation of acid groups. It can be used to obtain challenging copolymers and trigger degradation of polymer backbones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Sharath Chandra Mallojjala, Victor O. Nyagilo, Stephanie A. Corio, Alafate Adili, Anuradha Dagar, Kimberly A. Loyer, Daniel Seidel, Jennifer S. Hirschi
Summary: The mechanistic study of three intermolecular anti-Markovnikov alkene hydrofunctionalization reactions has provided detailed insights into the reaction pathways and rate-limiting steps. These findings can guide the development of asymmetric versions of these reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Fuchao Yu, Daniel A. Valles, Weijie Chen, Scott D. Daniel, Ion Ghiviriga, Daniel Seidel
Summary: Secondary alicyclic amines are converted to alpha-aminonitriles by adding TMSCN to their corresponding imines, which are generated in situ via the oxidation of amine-derived lithium amides with simple ketone oxidants. Amines with an existing a-substituent undergo regioselective alpha'-cyanation, even if the C-H bonds at that site are less activated. Amine alpha-arylation can be combined with alpha'-cyanation to produce difunctionalized products in a single step.
Article
Chemistry, Organic
Alafate Adili, Aniket V. V. Sole, Bishwaprava Das, Megan E. Matter, Daniel Seidel
Summary: In the presence of a thiourea-carboxylic acid catalyst, N-9-fluorenyltryptamines undergo highly enantioselective Pictet-Spengler reactions with a range of aldehydes. The reaction exhibits good compatibility with aromatic aldehydes, accepting diverse substituents at various positions on the ring. Electron-deficient tryptamines can also be used as substrates. Furthermore, the fluorenyl protecting group can be easily removed without affecting the enantioselectivity of the product.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Physical
Alafate Adili, John-Paul Webster, Chenfei Zhao, Sharath Chandra Mallojjala, Moises A. Romero-Reyes, Ion Ghiviriga, Khalil A. Abboud, Mathew J. Vetticatt, Daniel Seidel
Summary: The enantioselective oxa-Pictet-Spengler reactions of tryptophol with aldehydes were successfully conducted under weakly acidic conditions using a combination of indoline HCl salt and bisthiourea compound as catalysts. Mechanistic investigations determined the roles of both catalysts and confirmed the involvement of oxocarbenium ion intermediates, ruling out alternative scenarios. A stereochemical model derived from density functional theory calculations provided the basis for the development of a highly enantioselective stereodivergent variant with racemic tryptophol derivatives.
