Article
Chemistry, Organic
Javeed Ahmad Tali, Ravi Shankar
Summary: Here, we report an unprecedented protocol using ruthenium-catalyzed annulation for the synthesis of 6H-chromeno[4 ',3 ':4,5]imidazo[1,2-a]pyridin-6-one, and a new method for intramolecular chelation-assisted C-H activation to produce functionalized 2-(3-formylimidazo[1,2-a]pyridin-2-yl)phenyl acetate. Furthermore, a one-pot approach using ruthenium catalysis and formic acid has been developed for the gram-scale synthesis of bis(2-phenylimidazo[1,2-a]pyridin-3yl)methane (BIP) and the late-stage functionalization of zolimidine, a marketed drug, with good yield.
Article
Chemistry, Organic
Michael S. West, Alexis L. Gabbey, Malcolm P. Huestis, Sophie A. L. Rousseaux
Summary: A nickel-catalyzed reductive cross-coupling reaction has been developed for the synthesis of 1-arylcyclopropylamines. The method is efficient, fast, and tolerant of different functional groups.
Article
Chemistry, Physical
Lukasz Czieszowic, Beata Orlinska, Dawid Lisicki, Ewa Pankalla
Summary: An efficient method for the synthesis of 2-ethylhexanoic acid using oxygen or air in the presence of N-hydroxyphthalimide as a catalyst in isobutanol solvent has been developed. The method achieved a high selectivity of >99% for 2-ethylhexanoic acid and showed potential for implementation in industry due to its green oxidation process and mild reaction conditions. The use of isobutanol as a solvent is crucial for potential producers to utilize less valuable alcohol.
Article
Chemistry, Organic
Xiaoqin Ning, Yongke Chen, Fangdong Hu, Ying Xia
Summary: This study presents the palladium-catalyzed cross-coupling reactions of cyclobutanone-derived N-sulfonylhydrazones with aryl or benzyl halides, demonstrating that the metal carbene process and beta-hydride elimination can occur smoothly in strained ring systems to yield structurally diverse products. The preliminary success in asymmetric carbene coupling reactions in strained ring systems offers a promising route for the synthesis of enantioenriched four-membered-ring molecules.
Article
Chemistry, Multidisciplinary
Zijian Li, Wenxuan Sun, Xianxu Wang, Luyang Li, Yong Zhang, Chao Li
Summary: This method utilizes alcohols and aryl bromides as coupling partners, combining anodic preparation and nickel catalysis to efficiently construct C(sp(2))-C(sp(3)) bonds. The nickel-catalyzed paired electrolysis reaction showcases a broad substrate scope suitable for the synthesis of multifunctional compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Jun-Long Zhan, Lin Zhu, Wei Ren, Bing-Jie Wang, Xin-Ming Zhao, Xin-Ru Zhang, Xin-Yu Zhang, Yao-Qiang Xie
Summary: A feasible and umpolung strategy for synthesizing diverse beta-amino ketones was achieved through TEMPO mediated C-N coupling of cyclopropanols with nitrogen nucleophiles. Mechanism studies showed that enones derived from cyclopropanols are key intermediates and TEMPO plays multiple roles. This protocol offers broad substrate scope, good scalability, and good to excellent yields, providing an alternative approach to the synthesis of structurally important beta-amino ketone scaffolds under metal and additive-free conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Alexander Purtsas, Marco Rosenkranz, Evgenia Dmitrieva, Olga Kataeva, Hans-Joachim Knoelker
Summary: In this paper, the oxygenation and amination reactions of tertiary arylamines are described. The key steps of these coupling reactions involve iron-catalyzed oxidative C-O or C-N bond formation, which typically provide the desired products in high yields and with excellent regioselectivity. These transformations are carried out using hexadecafluorophthalocyanine-iron(II) (FePcF16) as catalyst, with the presence of an acid or base additive, and only require ambient air as the oxidant.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Yin-Bo Wan, Xiang-Ping Hu
Summary: A readily available and highly modular class of chiral P,N,N-ligands have been developed and successfully applied in the Ir-catalyzed asymmetric hydrogenation. These ligands exhibited excellent activity, enantioselectivity, and substrate tolerance, thus providing optically active compounds with high yields and enantioselectivities. This study demonstrates the utility of these ligands in diverse product transformation and the synthesis of biologically active compounds.
Article
Chemistry, Multidisciplinary
Bhushan A. Baviskar, Prashant V. Ajmire, Deshraj S. Chumbhale, Mohammad Sadat Khan, Vitthal G. Kuchake, Madhavi Singupuram, Purushottam R. Laddha
Summary: Research on transition metal catalysis, specifically exploring the applications of abundant first row transition elements for C-C coupling reactions, is rapidly advancing. The Suzuki-Miyaura coupling reaction, particularly catalyzed by nickel, has attracted significant interest from organic chemists in recent decades. However, the environmental concern of halogen waste has prompted the exploration of alternative electrophiles, such as carboxylic acid derivatives, phenol derivatives, and amides, to replace organic halides in traditional Suzuki coupling reactions. This strategy involves activating C-O and C-N bonds to form C-C coupling products. The current focus is on developing various Ni-based catalytic systems that activate C-O and C-N bonds to achieve successful Suzuki coupling reactions, with a recent emphasis on green metrics.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2023)
Article
Chemistry, Physical
Avishek Das, Nitin T. Patil
Summary: A ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction between aryl iodides and aliphatic alcohols is reported. The method is demonstrated to be useful for the synthesis of various aryl alkyl ethers, including complex biomolecules and medicinally relevant motifs. The importance of gold catalysis is highlighted in overcoming selectivity issues observed with other transition metal catalysts in C-O cross -coupling reactions.
Article
Chemistry, Physical
Avishek Das, Nitin T. Patil
Summary: Reported in this study is a ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction between aryl iodides and aliphatic alcohols. The usefulness of the method is demonstrated by successfully synthesizing a variety of aryl alkyl ethers, including complex biomolecules and medicinally relevant motifs. The importance of gold catalysis is highlighted by overcoming the selectivity issues commonly observed when other transition metals are used as catalysts for C-O cross-coupling reactions.
Article
Chemistry, Applied
Toru Hashimoto, Keisuke Shiota, Kei Funatsu, Yoshitaka Yamaguchi
Summary: A nickel-catalyzed cross-coupling reaction between aryl halides and primary or secondary aliphatic alcohols has been achieved using a bench-stable nickel complex supported by a monoanionic O,N,N-tridentate ligand. The reaction proceeds smoothly without the need for a phosphine ligand, giving moderate to good yields of alkyl aryl ethers.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Qiaerbati Adelibieke, Yi Ming Zhang, Xiu Juan Xu, Abudureheman Wusiman
Summary: An efficient TEMPO-catalyzed C-N cross-coupling amidation reaction has been developed using N-haloamides, allowing for the synthesis of electron-deficient tertiary aniline derivatives under milder conditions.
MONATSHEFTE FUR CHEMIE
(2023)
Article
Chemistry, Multidisciplinary
Jichao Xiao, Zhenning Li, John Montgomery
Summary: This study demonstrates a method using nickel catalysis and BiOx ligand for the reductive coupling of redox-active esters with aliphatic aldehydes to obtain silyl-protected secondary alcohols. The protocol is simple, mild, and tolerates a variety of functional groups, with potential mechanistic insights pointing towards a radical chain pathway.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Raymond F. Turro, Julie L. H. Wahlman, Z. Jaron Tong, Xiahe Chen, Miao Yang, Emily P. Chen, Xin Hong, Ryan G. Hadt, K. N. Houk, Yun-Fang Yang, Sarah E. Reisman
Summary: Mechanistic investigations of the Ni-catalyzed asymmetric reductive alkenylation of N-hydroxyphthalimide (NHP) esters and benzylic chlorides were conducted. The study revealed divergent mechanisms for these related transformations, with the mechanism of C(sp(3)) activation changing depending on the reactants used. Kinetic experiments showed that the rate of NHP ester reduction can be tuned by changing the Lewis acid. Spectroscopic studies and DFT calculations provided insights into the catalyst resting state and the origin of enantioinduction for the Ni-BOX catalyst.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
