Article
Chemistry, Multidisciplinary
Kuai Wang, Jiachang Chen, Wenfeng Liu, Wangqing Kong
Summary: The introduction of fluorine-containing groups into organic molecules can significantly affect their physical and chemical properties and has been widely used in drug discovery and development. In this study, a nickel-catalyzed asymmetric cyclization reaction was described, which enables the efficient synthesis of synthetically attractive 4-fluorovinyl-substituted 2-pyrrolidones. This protocol shows high chemo-, regio-, and enantioselectivities and can be utilized in the synthesis of the antiepileptic drug Seletracetam.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jiangyan Tian, Wendian Li, Ruihao Li, Lin He, Hui Lv
Summary: The nickel/(S)-t-Bu-PHOX complex catalyzed asymmetric arylative cyclization of N-alkynones has successfully delivered 1,2,3,6-tetrahydropyridines containing a chiral tertiary alcohol in high yields and excellent enantioselectivities, providing efficient access to chiral tetrahydropyridine and piperidine analogues.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Applied
Masami Kuriyama, Genki Maeda, Kazuya Kamata, Yusuke Kodama, Kosuke Yamamoto, Osamu Onomura
Summary: The nickel-catalyzed cross-coupling of bromodifluoromethylphosphonates with arylboron reagents was achieved using a 1,10-phenanthroline-type ligand. Functionalized and heterocycle-containing boroxines were suitable partners for this reaction, and the catalytic modification of biologically active molecules, such as fenofibrate and indomethacin, was successfully accomplished. Moreover, the gram-scale reaction proceeded smoothly with a high yield of desired product.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Shrikant D. Tambe, Cheol Hyeon Ka, Ho Seong Hwang, Jaehan Bae, Naeem Iqbal, Eun Jin Cho
Summary: The synthesis of highly functionalized chiral 3-pyrrolines is important for the production of natural and synthetic bioactive molecules. Previous methods using allenoates could not synthesize 3,4-disubstituted 3-pyrrolines. This study presents a novel approach to produce 2,3,4-trisubstituted chiral 3-pyrrolines through a highly stereoselective process using a Ni-II/Fc-i-PrPHOX catalytic system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Miriam Marchi, Giuseppe Gentile, Cristian Rosso, Michele Melchionna, Paolo Fornasiero, Giacomo Filippini, Maurizio Prato
Summary: Dual photocatalysis, combining Earth-abundant nickel-based catalytic systems with visible-light-activated photoredox catalysts, has become a powerful tool for functionalization of organic molecules under mild conditions. This relatively new branch of catalysis has inspired interdisciplinary research and established itself as a dominant trend in modern organic synthesis.
Article
Chemistry, Multidisciplinary
Harley Green, Stephen P. Argent, Hon Wai Lam
Summary: This study describes a novel domino reaction involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization onto acyclic ketones to yield chiral tertiary-alcohol-containing products with high enantioselectivities. The reversible E/Z isomerization of the alkenylnickel intermediates allows overall anti-arylmetallative cyclization to occur, producing products with ring systems similar to certain diarylindolizidine alkaloids.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Fengjuan Chen, Luo Liu, Wei Zeng
Summary: Compared with all-carbon parent compounds, incorporating Silicon into carboskeletons gives sila-analogues unique biological activity and physical-chemical properties. Silacycles have shown promising potential in biological chemistry, pharmaceuticals industry, and material chemistry. Therefore, the development of efficient methods to assemble versatile silacycles has been a topic of increasing concern. This review summarizes recent advances in the synthesis of silacycle-system, including transition metal-catalytic and photocatalytic strategies using various starting materials. The mechanistic aspects and features of these reaction methodologies are also highlighted.
FRONTIERS IN CHEMISTRY
(2023)
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Chi Bong Eric Chao, Stephen G. Pyne, Christopher J. T. Hyland, Richmond Lee
Summary: Density functional theory has been used to elucidate the mechanistic details of arylative cyclization reactions with arylboronic acids. The modeling results are in agreement with experimental observations and explain the high diastereo- and enantioselectivity at high reaction temperature. Additionally, a novel mechanism for base-free organoboron transmetalation has been revealed.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Zhenhua Zhang, Julius B. Stueckrath, Stefan Grimme, Andreas Gansaeuer
Summary: Cp2Ti(TFA) is a versatile catalyst for the [2+2] cycloaddition of bisenones through inner-sphere electron transfer, with a unique 5-exo step as the rate-determining step followed by a favorable 4-exo cyclization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Bing-Bing Wu, Jie Xu, Qian Gao, Kang-Jie Bian, Guo-Kai Liu, Xi-Sheng Wang
Summary: In this study, a general and efficient method for preparing diverse aliphatic monofluorides was reported using monofluoroalkyl triflate as the synthetic scaffold. The broad utility of this monofluoroalkylating reagent was demonstrated through nickel-catalyzed hydromonofluoroalkylation and copper-catalyzed C-C bond formation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Si-Chen Tao, Fan-Cheng Meng, Tie Wang, Yan-Long Zheng
Summary: A new, efficient, and practical method for three-component arylative coupling reactions has been developed using nickel catalysis. This reaction produces diverse Z-selective tetrasubstituted allylic alcohols without the need for aggressive organometallic reagents or reductants. The utility of this method is demonstrated through the synthesis of various biologically active molecular derivatives.
Article
Chemistry, Organic
Fang-Yuan Nie, Yi-Ping Cai, Qin-Hua Song
Summary: In this paper, a photocatalyst-free and visible light-driven decarboxylative alkylation of pyridinaldehydes is developed. The reactions are initiated by photoinduced single electron transfer and successfully convert pyridinaldehydes and 2-quinolinaldehydes to the corresponding ketones. Besides, this method also enables two other transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Ravinder Kumar, Yugam Khanna, Parul Kaushik, Raj Kamal, Shiwani Khokhar
Summary: This review summarizes the impressive breakthroughs in organic synthesis, specifically the inter/intra-molecular vicinal diamination of alkenes with electron-rich or deficient nitrogen sources. These breakthroughs predominantly involve iodine-based reagents/catalysts, which have gained interest due to their flexibility, non-toxicity, and environmental friendliness, resulting in a wide variety of useful organic compounds. The information collected also highlights the role of catalyst, oxidant, substrate scope, synthetic applications, and their limitations, with proposed mechanistic pathways to determine key factors governing regioselectivity, enantioselectivity, and diastereoselectivity ratios.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Pawan S. Dhote, Swapnil V. Halnor, Chepuri V. Ramana
Summary: The article discusses the gold-catalysed intramolecular redox cyclization of o-alkynylnitrobenzens, highlighting its importance and potential for further research in metal catalysis. It also touches upon the idea of generating alpha-oxo gold carbenes via oxygen transfer to alkynes, establishing another significant aspect in gold catalysis.
Article
Chemistry, Multidisciplinary
Somnath Narayan Karad, Heena Panchal, Christopher Clarke, William Lewis, Hon Wai Lam
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Thi Le Nhon Nguyen, Celia A. Incerti-Pradillos, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Yunfei Luo, Steven M. Wales, Stamatis E. Korkis, Iain D. Roy, William Lewis, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Johnathon D. Dooley, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Correction
Chemistry, Multidisciplinary
Alistair Groves, Jose I. Martinez, Joshua J. Smith, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Harley Green, Stephen P. Argent, Hon Wai Lam
Summary: This study describes a novel domino reaction involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization onto acyclic ketones to yield chiral tertiary-alcohol-containing products with high enantioselectivities. The reversible E/Z isomerization of the alkenylnickel intermediates allows overall anti-arylmetallative cyclization to occur, producing products with ring systems similar to certain diarylindolizidine alkaloids.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Luke O'Brien, Stephen P. Argent, Kristaps Ermanis, Hon Wai Lam
Summary: Gold(I)-catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates were studied. The reactions showed high selectivity and provided a variety of functionalized 1,4-dihydropyridines and 1,4-dihydroquinolines. Experimental evidence and density functional theory calculations revealed the mechanistic insights.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Dmitry Gorbachev, Elliot Smith, Stephen P. Argent, Graham N. Newton, Hon Wai Lam
Summary: This study describes the synthesis of new morphinan opioids by adding photochemically generated carbon-centered radicals to substrates containing an enone in the morphinan C-ring. By using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer photocatalyst, diverse radical donors can be used to prepare a variety of C8-functionalized morphinan opioids. This work demonstrates the feasibility of late-stage modification of complex, highly functionalized substrates.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Simone M. Gillbard, Harley Green, Stephen P. Argent, Hon Wai Lam
Summary: Enantioselective nickel-catalyzed reactions of (hetero)arylboronic acids or alkenylboronic acids with substrates containing an alkyne tethered to various acyclic electron-deficient alkenes are discussed in this study.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Alistair Groves, Jinwei Sun, Hal R. I. Parke, Michael Callingham, Stephen P. Argent, Laurence J. Taylor, Hon Wai Lam
Article
Chemistry, Multidisciplinary
Riccardo Di Sanza, Thi Le Nhon Nguyen, Naeem Iqbal, Stephen P. Argent, William Lewis, Hon Wai Lam
Article
Chemistry, Multidisciplinary
Luke O'Brien, Somnath Narayan Karad, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Rebecca E. Ruscoe, Michael Callingham, Joshua A. Baker, Stamatis E. Korkis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Heena Panchal, Christopher Clarke, Charles Bell, Somnath Narayan Karad, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2018)
