Article
Chemistry, Organic
Chungang Li, Mingli Zhong, Zheng Zeng, Yiqiu Deng, Lanyu Li
Summary: An iridium-catalyzed hydrogen transfer strategy allows for the straightforward synthesis of tetrahydropyridine derivatives, offering high efficiency and environmental friendliness.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Samantha L. Goldschmid, Nicholas Eng Soon Tay, Candice L. Joe, Brendan C. Lainhart, Trevor C. Sherwood, Eric M. Simmons, Melda Sezen-Edmonds, Tomislav Rovis
Summary: Aryl amination plays a crucial role in medicinal, process, and materials chemistry. Blue-light-driven metallaphotoredox catalysis is a valuable tool for C-N cross-coupling, but its limited penetration through reaction media and the formation of unwanted side-products pose challenges for industrial scalability. Using low-energy light, such as deep red or near-infrared, can enhance penetration and suppress unwanted reactions, leading to an enhanced scope of aryl bromides and amine-based nucleophiles.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Shuaishuai Wang, Tingrui Li, Chengyihan Gu, Jie Han, Chuan-Gang Zhao, Chengjian Zhu, Hairen Tan, Jin Xie
Summary: This article reports on an iron-catalyzed reaction for efficient construction of aromatic tertiary amines, which is important in drug discovery and organic chemistry. The reaction employs a radical tandem C-N coupling strategy and can synthesize nonsymmetric aromatic tertiary amines under mild conditions.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Dong Sun Kim, Hong Geun Lee
Summary: This rare synthetic strategy utilizes a copper-catalyzed oxidative cross-coupling to form C(sp(3))-N bonds, allowing the preparation of tertiary sulfonamides. The method is tolerant of a wide range of functional groups under mild conditions and relies on the additive effects of silanol and NaIO4.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Bastian L. Springer, Kristina Holzschneider, Fabian Mohr, Stefan F. Kirsch
Summary: A new synthetic route for phenanthro[9,10-d]imidazoles is reported. The target compounds were synthesized through the aminolysis of readily accessible 10,10-diazidophenanthren-9(10H)-one with nucleophilic amines, followed by a self-condensation. X-ray single crystallography was used to determine the molecular structures, and the optical properties of the material were described.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Gen Li, Steven P. Miller, Alexander T. Radosevich
Summary: The reported method utilizes an organophosphorus catalyst and hydrosilane to drive the cross-selective intermolecular N-N reductive coupling of nitroarenes and anilines, with good chemoselectivity and functional group tolerance. Mechanistic investigations support an autotandem catalytic reaction cascade involving two sequential reduction events to produce the desired N-N bond.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Guang Yang, Zhicheng Xiong, Hongsheng Nie, Meiqin He, Qiong Feng, Xuan Li, Huabin Huang, Shoucai Wang, Fanghua Ji, Guangbin Jiang
Summary: With control by N1-substituents, switchable divergent C-H functionalization reaction of quinoxalin-2(1H)-ones was achieved for the synthesis of (Z)-enaminones and furo[2,3-b]quinoxalines using copper catalyst and oxidant. The method features mild reaction conditions, readily available materials, and a broad substrate scope, and the desired products showed excellent antitumor activity against A549, HepG-2, MCF-7, and HeLa cells.
Article
Chemistry, Multidisciplinary
Xiao-Yang Dong, Zhong-Liang Li, Qiang-Shuai Gu, Xin-Yuan Liu
Summary: This article mainly introduces the research progress on enantioconvergent radical cross-coupling reactions. Compared with chiral nickel catalysts, the study of copper-catalyzed enantioconvergent radical cross-coupling is less explored, primarily due to the weak reducing capability of copper. In recent years, researchers have been dedicated to developing chiral ligands for copper-catalyzed enantioconvergent radical cross-coupling to address the issues of enantiocontrol and reaction initiation speed.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Mauro Mato, Davide Spinnato, Markus Leutzsch, Hye Won Moon, Edward J. J. Reijerse, Josep Cornella
Summary: This article explores the use of a low-valency bismuth complex to undergo oxidative addition reactions with redox-active alkyl-radical precursors, resembling the behavior of transition metals. Mechanistic investigations of this reactivity lead to the development of a bismuth-catalyzed C(sp(3))-N cross-coupling reaction that operates under mild conditions and accommodates synthetically relevant NH-heterocycles as coupling partners.
Article
Chemistry, Organic
Dellamol Sebastian, Patrick H. Willoughby, Mahesh K. Lakshman
Summary: Cross-dehydrogenative coupling reactions were used to alkylate 4(3H)-quinazolinones with ethers and amides, with catalytic n-Bu4NI and t-BuOOH as oxidants. The reactions with amides were the first examples under these conditions. Mechanistic insights were obtained through inter- and intramolecular competitive experiments with protio and deuterio reactants, as well as radical inhibition experiments. Understanding of the relative reactivities of ethers was also achieved through pairwise competitions with 4(3H)-quinazolinone.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Zhenwei Ni, Rosa Padilla, Rajib Pramanick, Mike S. B. Jorgensen, Martin Nielsen
Summary: A base-free, acceptorless dehydrogenative coupling of ethanol to ethyl acetate is achieved using a pincer complex ((PNP)-P-Ph)RuH(BH4)(CO) (0.25 mol%) and m-xylene as the co-solvent. The catalysis shows excellent conversion and yield of >99% after 24 h at 120 degrees C. The scaled-up reaction is also effective under similar conditions.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Jessica C. Bieniek, Boris Mashtakov, Dieter Schollmeyer, Siegfried R. Waldvogel
Summary: This study presents an electrocatalytic method using hypervalent iodine(III) as a mediator to synthesize 1H-N-aryl-3,4-dihydroquinolin-2-ones by C-N bond formation. The method features a low catalyst loading, recycling of the solvent, and is a sustainable alternative to conventional approaches.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Karli R. Holman, Allison M. Stanko, Matthieu J. R. Richter, Sean S. Feng, Mahideremariyam N. Gessesse, Sarah E. Reisman
Summary: In this study, radical and transition metal-catalyzed cascade cyclization strategies were explored for the synthesis of the tetracyclic core of the augustamine-type Amaryllidaceae alkaloids. The successful synthesis of noraugustamine and the development of an oxidative Heck/aza-Wacker cascade that forms multiple bonds and a quaternary carbon center in a single step were achieved.
Article
Chemistry, Organic
Vladimir Motornov, Petr Beier
Summary: NH-1,2,3-Triazoles undergo ring cleavage in reactions with fluorinated acid anhydrides and can be used for the synthesis of fluoroalkylated compounds.
Article
Chemistry, Multidisciplinary
Lei Yang, Maolin Sun, Liming Cao, Chaoming Liang, Jiasheng Yang, Junjun Yi, Ruihua Cheng, Yueyue Ma, Jinxing Ye
Summary: A three-component reductive coupling reaction has been developed under electrochemical conditions, involving aldehydes, amines, and cyanopyridines. In situ generation of imine and cyanopyridine allows for simultaneous single-electron reduction at the cathode, leading to the formation of diarylmethylamines through radical coupling. This method enables the modular synthesis of various secondary and tertiary amines with broad functional group compatibility.
CHEMICAL COMMUNICATIONS
(2022)
