Article
Chemistry, Multidisciplinary
Miki B. Kurosawa, Kenta Kato, Kei Muto, Junichiro Yamaguchi
Summary: A deoxygenative transformation method was developed for the synthesis of multiply arylated alkanes from various diarylketones. The method involves a phospha-Brook rearrangement of diarylketones by reacting with diphenylphosphine oxide, followed by palladium-catalyzed cross-couplings or a Friedel-Crafts type alkylation. The method also enables the one-pot conversion from arylcarboxylic acids to diarylmethanes and tetraarylethanes, as well as the synthesis of tetraarylmethane and triphenylethane using sequential coupling reactions.
Article
Biochemistry & Molecular Biology
Vitor A. S. Almodovar, Augusto C. Tome
Summary: This article presents a convenient two-step synthesis of various DPP dyes from Pigment Red 254, showing large Stokes shifts and high fluorescence quantum yields, which are important properties for their potential use in technical and biological applications.
Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
Article
Chemistry, Physical
Masoumeh Beiranvand, Davood Habibi
Summary: In this study, the mesoporous silica SBA-15 (SBA) was modified by a tetra-urea (TU) ligand to prepare the SBA@TU@Pd(0) nano-structured reduced catalyst. The catalytic activity of SBA@TU@Pd(0) was successfully studied in the Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions, showing short reaction times and high yields. The non-reduced nano-catalyst SBA@TU@Pd(II) also exhibited similar reaction yields but longer reaction times.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Julia E. Borowski, Samuel H. Newman-Stonebraker, Abigail G. Doyle
Summary: A comparison study of mono- and bisphosphine ligands in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions revealed that monophosphines exhibit higher reactivity, particularly with electronically deactivated and sterically hindered substrates. Mechanistic experiments showed that monoligated (P1Ni) species accelerate the organometallic steps of the catalytic cycle, while bisligated (P2Ni) species prevent off-cycle reactions and catalyst poisoning by heterocyclic motifs. These findings provide guidelines for ligand selection against challenging substrates and future ligand design tailored to the mechanistic demands of Ni-catalyzed cross-coupling reactions.
Article
Chemistry, Physical
Yiyang Zhang, Hong Sun, Yonghuai Yang, Haofei Li, Yaocheng Shi, Lei Yu
Summary: The catalytic activities of palladium nanoparticles on a polyaniline support were improved by tungsten doping, resulting in a significantly increased catalyst turnover number (>10(4)) for the Suzuki-Miyaura coupling reaction. Characterization of the materials showed that tungsten doping improved the micro-morphology, leading to more efficient absorption of reactants. Additionally, tungsten facilitated stabilization of Pd(0) species and the transmetallation step, both crucial for the catalytic reaction. Therefore, Pd/W@PANI engineering material may serve as a highly efficient heterogeneous catalyst in the pharmaceutical industry.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Inorganic & Nuclear
Jairus L. Lamola, Joy C. Shilubana, Lonwabo Ngodwana, Banele Vatsha, Adedapo S. Adeyinka, Munaka C. Maumela, Cedric W. Holzapfel, Edwin M. Mmutlane
Summary: Researchers have developed two new Pd(II) complexes, suitable for Suzuki-Miyaura cross-coupling reactions. These active catalysts, formed by aminophosphines, show good performance in coupling reactions of aryl bromides and chlorides.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jie Xu, Samantha Grosslight, Kyle A. Mack, Sierra C. Nguyen, Kyle Clagg, Ngiap-Kie Lim, Jacob C. Timmerman, Jeff Shen, Nicholas A. White, Lauren E. Sirois, Chong Han, Haiming Zhang, Matthew S. Sigman, Francis Gosselin
Summary: An efficient asymmetric synthesis of a potent KRAS G12C covalent inhibitor, GDC-6036, was reported. The synthesis involved a highly selective Negishi coupling and a series of reaction sequences, leading to the desired compound with a 40% overall yield from the starting materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Changyue Ren, Hang Zhang, Zhengjun Chen, Jie Gao, Mingyan Yang, Zeli Yuan, Xinmin Li
Summary: This study presents a Pd/C catalyzed Suzuki-Miyaura reaction in water extract of suaeda salsa, which does not require external phosphine ligand, base, and organic solvent. The reaction shows a broad substrate scope and high purity of the products can be obtained.
Article
Nanoscience & Nanotechnology
Soniya Agarwal, Shyamolima Bairagi, Masshuda Madni Khatun, Kalyanjyoti Deori
Summary: A surfactant free solid solution of NiZn with a hierarchical architecture was synthesized using a one-pot colloidal approach. The formation of hierarchical crystal growth and atomic level alloying of metals was confirmed through field emission scanning electron microscopy and transmission electron microscopy-energy-dispersive X-ray data. This well-alloyed, magnetically separable, non-noble metal-based solid solution has shown potential to replace palladium-based catalysts in Suzuki-Miyaura cross-coupling reactions. The nanostructured catalyst, formed by the assembly of triangular spiked and sheet-like structures, is stable and outperforms most reported transition metal-based catalysts.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Inorganic & Nuclear
Zhifo Guo, Xiangyang Lei
Summary: The new catalytic system using Ni(NO3)(2)center dot 6H(2)O as catalyst and a pincer pyrrole-functionalized N-heterocyclic carbene as ligand showed high efficiency in Suzuki-Miyaura cross-coupling reactions of aryl iodides with arylboronic acids, yielding high isolated yields of coupling products in short reaction times. The system worked well with aryl iodides bearing electron-donating or electron-withdrawing groups and arylboronic acids with electron-donating groups, while steric effects were observed for both aryl iodides and arylboronic acids.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jin Zhang, Pei Zhang, Lei Shao, Ruihong Wang, Yangmin Ma, Michal Szostak
Summary: A highly chemoselective, solvent-free mechanochemical strategy for the cross-coupling of amides by N-C bond activation has been reported. The method shows excellent selectivity, functional group tolerance, and can be applied for late-stage functionalization of complex molecules. This extends the repertoire of N-C bond interconversions to solid-state environmentally friendly mechanochemical methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Linda Pudnika, Ilona Domraceva, Thomas Werner, Raivis Zalubovskis, Aiga Grandane
Summary: The study successfully synthesized compounds with potential biological activity containing benzoxepinone core structures through a simple and efficient synthetic route, and obtained diverse derivatives through late stage modification. This method is highly applicable for high throughput applications and provides a convenient pathway for further functionalization.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Zahra Khorsandi, Abdol R. Hajipour, Mohamad Reza Sarfjoo, Rajender S. Varma
Summary: The nano-catalytic system described consists of magnetic nanoparticles as the core and edible natural ligands with functional groups as supports for cobalt species. It shows good catalytic activity in C-N cross-coupling reactions and demonstrates excellent efficiency and versatility in an array of coupling reactions. The system is easily accessible and has good recyclability for potential future applications.
Article
Chemistry, Applied
Nadezhda A. Lagoda, Elizaveta Larina, Elena V. Vidyaeva, Anna A. Kurokhtina, Alexander F. Schmidt
Summary: This study distinguishes between the homogeneous and heterogeneous catalytic mechanisms of Pd catalytic systems in the Suzuki-Miyaura reaction, providing convincing evidence for reactions proceeding simultaneously through both mechanisms. The use of ligand-free conditions suggests that the reaction proceeds in the solution phase through a homogeneous mechanism even when heterogeneous precursors are used, based on differential selectivity under competition conditions.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Multidisciplinary Sciences
Ming Joo Koh, R. Kashif M. Khan, Sebastian Torker, Miao Yu, Malte S. Mikus, Amir H. Hoveyda
Article
Chemistry, Inorganic & Nuclear
Sebastian Torker, Ming Joo Koh, R. Kashif M. Khan, Amir H. Hoveyda
Article
Chemistry, Multidisciplinary
Ming Joo Koh, R. Kashif M. Khan, Sebastian Torker, Amir H. Hoveyda
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Multidisciplinary
R. Kashif M. Khan, Yang Zhao, Tal D. Scully, Stephen L. Buchwald
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Hien-Ouang Do, Rana M. Kashif Khan, Olafs Daugulis
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2008)
Article
Chemistry, Multidisciplinary
R. Kashif M. Khan, Robert V. O'Brien, Sebastian Torker, Bo Li, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Multidisciplinary
R. Kashif M. Khan, Adil R. Zhugralin, Sebastian Torker, Robert V. O'Brien, Pamela J. Lombardi, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Multidisciplinary
R. Kashif M. Khan, Sebastian Torker, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2013)
Article
Chemistry, Multidisciplinary
Sebastian Torker, R. Kashif M. Khan, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Multidisciplinary
R. Kashif M. Khan, Sebastian Torker, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Physical
Guoqian Jiang, Akira Baba, Hiroshi Ikarashi, Risheng Xu, Jason Locklin, Khan Rana Kashif, Kazunari Shinbo, Keizo Kato, Futao Kaneko, Rigoberto Advincula
JOURNAL OF PHYSICAL CHEMISTRY C
(2007)
