Article
Chemistry, Multidisciplinary
Mandapati Bhargava Reddy, Sakthivel Prabhu, Ramasamy Anandhan
Summary: An unprecedented reductive hydroamidative/hydroquinazolinative cascade cyclization of o-alkynylated derivatives was achieved via proton-coupled electron transfer (PCET) under electrolysis. In a single step, the rapid assembly of isoindolinones and novel isoindole-fused quinazolinones were achieved through electrolysis by the hydroamidation of amidyl/quinazolinone aminyl radicals with C-C triple bond addition via 5-exo-dig cyclization followed by olefinic reduction without external reductants. Control and cyclic voltammetry experiments support a mechanistic explanation of the electrochemical cascade, and these experiments indicate that the electrolyte is the source of hydrogen for the olefin reduction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Mizuki Seki, Kazuhiro Yoshida
Summary: A new chiral rhodium catalyst was synthesized and fully characterized, showing good catalytic activity and enantioselectivity in asymmetric reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yang Gao, Yushan Cui, Yanping Huo, Jinhong Chen, Minwei She, Xianwei Li, Qian Chen, Xiao-Qiang Hu
Summary: A nickel-catalyzed polarity-reversed hydroamination of olefins has been developed, providing a convenient route to N-alkyl-2-aminobenzophenones intermediates. This method is compatible with a wide range of olefins and anthranils, delivering the desired amines in high yields, making it applicable for organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Cong Wang, Tiezheng Jia
Summary: This study presents a mild photocatalytic anti-Markovnikov hydroamination of alkenes to construct N-alkylated sulfoximines with broad substrate tolerance. The method provides a new synthetic strategy for drug discovery and agrochemistry.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Manideepa Sengupta, Tuhin Suvra Khan, Subhasis Das, Gurmeet Singh, Ravi Kumar, Dibyendu Bhattacharya, M. Ali Haider, Sk Manirul Islam, Ankur Bordoloi
Summary: In this study, Rh2O3 nanoparticles confined in silica meso-channels were prepared and showed excellent catalytic activity and selectivity in the direct addition of piperidine to ethylene. The superior activity of the nanoparticles over large particles was attributed to the binding mode of ethylene with the Rh species.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Lingpu Meng, Jingjie Yang, Mei Duan, You Wang, Shaolin Zhu
Summary: Regio- and enantioselective hydroarylamination, hydroalkylamination and hydroamidation of styrenes have been developed using NiH catalysis with a simple bioxazoline ligand under mild conditions. A variety of enantioenriched benzylic arylamines, alkylamines and amides can be easily accessed by employing nitroarenes, hydroxylamines and dioxazolones as amination reagents. Chiral induction in these reactions is proposed to proceed through an enantiodifferentiating syn-hydronickellation step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
An T. Ho, Seth C. Ensign, Evan P. Vanable, David Portillo, Jenna N. Humke, Gregory D. Kortman, Kami L. Hull
Summary: The Ir-catalyzed regioselective hydroamination of allyl amines and the catalyst-controlled regiodivergent hydroamination of homoallylic amines with aniline nucleophiles have been reported. These reactions can selectively synthesize diamines at different positions, and exhibit good reaction yields.
Article
Chemistry, Physical
Leipeng Xie, Jimin Liang, Haohao Bai, Xuanyu Liu, Xiao Meng, Yuan-Qing Xu, Zhong-Yan Cao, Chao Wang
Summary: In this paper, a ligand-controlled, directing-group-assisted strategy was reported to promote NiH-catalyzed site-selective hydroamination of unactivated alkenes. Proper bidentate nitrogen-containing ligands were used to achieve good-to-excellent regioselectivity for the synthesis of 1,1-, 1,2-, and 1,3-diamines from the same substrates. Various O-benzoylhydroxylamine electrophiles with different functional groups can be installed via Ni migration or nonmigration. These protocols provide a method for the enantioselective synthesis of valuable 1,2-diamines and 1,3-diamines.
Article
Chemistry, Organic
Kadiyala Sagar, Tapas R. Pradhan, Abdikani Omar Farah, Henry R. Wise, Bhailal C. Merja, Malempati Srimannarayana, Paul Ha-Yeon Cheong, Jin Kyoon Park
Summary: The assistance of 1,1,1,3,3,3-hexafluoro-2-propanol enables the metal-free synthesis of 1,3-diamines via regioselective intermolecular interception of amines. N-chemoselectivity and regioselectivity are achieved for a wide range of substrates. Mechanistic studies and computational calculations provide insights into the reaction pathway and selectivity control.
Article
Chemistry, Multidisciplinary
Alex J. Chinn, Kassandra Sedillo, Abigail G. Doyle
Summary: Novel strategies for accessing radicals from common feedstock chemicals have the potential to significantly impact synthetic chemistry. A dual phosphine and photoredox catalytic system has been developed to directly form sulfonamidyl radicals from primary sulfonamides, enabling an intermolecular anti-Markovnikov hydroamination reaction of unactivated olefins. This innovative approach allows for the preparation of structurally diverse secondary sulfonamides in good to excellent yields under mild conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Inorganic & Nuclear
Andrew T. Henry, Dana A. R. Nanan, Kim M. Baines
Summary: Various applications of bis(catecholato)germanes in catalysis were investigated, including hydrosilylation of benzaldehydes, hydroboration of phenylacetylene derivatives, and Friedel-Crafts alkylation using arylalkenes and either diphenylamine or anisole. Additionally, the catalytic activity of bis(catecholato)germanes with weak donor ligands in the oligomerization of α-methylstyrene was further studied, leading to the observation of trimer species formation in DCM. VTNA and Hammett analyses were performed, and an updated mechanism for bis(catecholato)germane catalysis was proposed.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Jeymy T. Sarmiento, Maria Carcel, Carmen Ramirez de Arellano, Teresa Varea, Gregorio Asensio, Andrea Olmos
Summary: In this study, alpha-chloromethylketimines have been synthesized through a gold-catalyzed hydroamination reaction of aromatic and aliphatic 1-chloroalkynes with aromatic amines. This method allows the preparation and spectroscopic characterization of alpha-chloromethylketimines with high purity, complete conversion, and atom economy. The synthetic usefulness of this methodology has been demonstrated through the preparation of beta-chloroamines and indoles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lu Wang, Minxu Shi, Xiaoping Chen, Nicholas Su, Weili Luo, Xiaheng Zhang
Summary: In this study, aromatic N-heterocyclic radicals were generated and utilized for the functionalization of unactivated alkenes, leading to the efficient synthesis of alkylated N-heterocyclic amines with medicinal relevance. This approach offers a novel retrosynthetic disconnection for the synthesis of therapeutic molecules and can be extended to the synthesis of densely functionalized heterocyclic amines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jeymy T. T. Sarmiento, Maria Carcel, Carmen Ramirez de Arellano, Teresa Varea, Gregorio Asensio, Andrea Olmos
Summary: α-Chloromethylketimines have been synthesized through a gold-catalyzed hydroamination reaction of aromatic amines with aromatic and aliphatic 1-chloroalkynes. This method allows for the preparation and spectroscopic characterization of α-chloromethylketimines, as well as the synthesis of β-chloroamines and indoles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Nora Jannsen, Cornelia Pribbenow, Carmen Selle, Hans-Joachim Drexler, Marc-Andre Mueller, Jonathan A. Medlock, Werner Bonrath, Detlef Heller
Summary: An efficient and highly selective semi-hydrogenation of terminal alkynes to alkenes has been achieved using neutral dimeric rhodium(I) complexes. The results show excellent selectivity and no deactivation or reduction in selectivity, indicating the potential industrial application of homogeneous rhodium complexes in the semi-hydrogenation of terminal alkynes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Hind Mamlouk, Jakkrit Suriboot, Praveen Kumar Manyam, Ahmed AlYazidi, David E. Bergbreiter, Sherzod T. Madrahimov
CATALYSIS SCIENCE & TECHNOLOGY
(2018)
Article
Chemistry, Multidisciplinary
Sherzod T. Madrahimov, Tulay A. Atesin, Olga Karagiaridi, Amy A. Sarjeant, Omar K. Farha, Joseph T. Hupp, SonBinh T. Nguyen
CRYSTAL GROWTH & DESIGN
(2014)
Article
Chemistry, Multidisciplinary
Sherzod T. Madrahimov, Dean Markovic, John F. Hartwig
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2009)
Article
Chemistry, Multidisciplinary
Sherzod T. Madrahimov, John F. Hartwig
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Nanoscience & Nanotechnology
Palani Elumalai, Hind Mamlouk, Wubulikasimu Yiming, Liang Feng, Shuai Yuan, Hong-Cai Zhou, Sherzod T. Madrahimov
ACS APPLIED MATERIALS & INTERFACES
(2018)
Article
Chemistry, Physical
Liang Feng, Ying Wang, Shuai Yuan, Kun-Yu Wang, Jia-Luo Li, Gregory S. Day, Di Qiu, Lin Cheng, Wen-Miao Chen, Sherzod T. Madrahimov, Hong-Cai Zhou
Article
Chemistry, Multidisciplinary
Matthew Du, Ananya M. Agrawal, Sanjiban Chakraborty, Sergio J. Garibay, Rungmai Limvorapitux, Baikleem Choi, Sherzod T. Madrahimov, SonBinh T. Nguyen
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2019)
Article
Nanoscience & Nanotechnology
Hind Mamlouk, Palani Elumalai, Manyam Praveen Kumar, Farida H. Aidoudi, Ashfaq A. Bengali, Sherzod T. Madrahimov
ACS APPLIED MATERIALS & INTERFACES
(2020)
Article
Nanoscience & Nanotechnology
Wenmiao Chen, Peiyu Cai, Palani Elumalai, Peng Zhang, Liang Feng, Ma'moun Al-Rawashdeh, Sherzod T. Madrahimov, Hong-Cai Zhou
Summary: The study demonstrates a method of direct Pd coordination in MOF catalysts for Suzuki-Miyaura coupling reaction through post-synthetic modification. Results show the heterogeneous nature, stability, and efficiency of MOF catalysts in continuous reactions under microflow conditions.
ACS APPLIED MATERIALS & INTERFACES
(2021)