Review
Chemistry, Multidisciplinary
Jiarong Shi, Lianggui Li, Yang Li
Summary: Arynes are highly active organic intermediates used in the rapid synthesis of substituted arenes, with o-silylaryl triflates being the most frequently employed precursors. The resurgence in aryne chemistry over the past 20 years is largely attributed to the widespread use of Kobayashi's method, which involves fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group. This review provides an overview of the history, achievements, and applications of Kobayashi's method in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.
Article
Chemistry, Inorganic & Nuclear
Brylon N. Denman, Erin E. Plasek, Courtney C. Roberts
Summary: This article explores a method to achieve regioselectivity in metal-catalyzed aryne difunctionalization through catalyst control.
Article
Chemistry, Organic
Biao Guo, Jiaying Lv, Le Lu, Ruimao Hua
Summary: A novel method for constructing the cyclopenta[c]quinoline ring has been developed, which involves the cyclization of 3-bromoindoles with internal alkynes in the presence of palladium. The mechanism of the formation of the cyclopenta[c]quinoline ring is proposed to proceed via a double [1,5] carbonsigmatropic rearrangement of the spirocyclic cyclopentadiene intermediate, generated from the cyclization of 3-bromoindoles with internal alkynes. This study also presents a new ring-expansion reaction of the pyrrole ring to pyridine via one carbon insertion into the C2-C3 bond of indoles, providing a simple and distinct route for constructing tricyclic fused-quinoline derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sunil Kumar Sunnam, Jitendra D. Belani
Summary: Recent research has explored arylation via ortho C-H activation with the aid of directing groups, leading to the development of a palladium-catalyzed C-H arylation using 8-aminoquinoline as a bidentate directing group. This method selectively provides C-H arylation products, unlike previous methods where cyclization to isoquinolones was observed. Additionally, sequential C-H functionalization was observed under specific conditions, leading to C-H olefination with the aryl group introduced from the aryne precursor.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Daigo Hayashi, Tomohiro Tsuda, Ryo Shintani
Summary: A palladium-catalyzed skeletal rearrangement has been developed to synthesize highly fused tetrahydrophenanthrosilole derivatives via bond exchange. The reaction conditions can be tuned to produce different products, fused dihydrodibenzosilepin derivatives.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Tianyu Zhang, Zhenkun Yang, Dapeng Zhou, Fuliang Meng, Zhengyu Han, Hai Huang
Summary: This work presents a new catalytic and highly chemoselective cross-Claisen condensation of esters, using silyl ketene acetals as carbonic nucleophiles. The process offers mild conditions and good functional group tolerance compared to traditional Claisen condensation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Mengyang Shen, Jie Zhao, Yuanshuang Xu, Xinying Zhang, Xuesen Fan
Summary: This novel synthesis method of dihydroquinolinone derivatives involves an unprecedented cascade reaction, which includes the in-situ formation of aryne and its addition with pyrazolidinone, followed by N-N bond cleavage and intramolecular C-C bond formation. Compared to existing methods, this protocol offers advantages such as multiple transformations in one pot, a broad substrate scope, mild reaction conditions, and good tolerance of various functional groups. Additionally, the products obtained from this method demonstrated significant in vitro antiproliferative activity in selected human cancer cell lines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kun Liu, Armido Studer
Summary: This study presents a method for the formal beta-C-H arylation of aldehydes and ketones using cooperative nickel and photoredox catalysis, which exhibits wide scope and tolerance towards functional groups. Additionally, it enables beta-alkenylation, beta-alkynylation, and beta-acylation of aldehydes under similar conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Nikoleta Spiliopoulou, Christoforos G. Kokotos
Summary: A new photochemical approach for the synthesis of symmetrical and non-symmetrical disulfides is described, utilizing mild, inexpensive and green conditions. The method involves the use of phenylglyoxylic acid as the photoinitiator, household bulbs as the light source, and a simple inorganic salt as the additive, resulting in excellent yields of the products.
Article
Chemistry, Multidisciplinary
Bo Yang, Jihui Gao, Xingfa Tan, Yicong Ge, Chuan He
Summary: A new type of chiral silyl ligand is developed, enabling the first iridium-catalyzed atroposelective intermolecular C-H silylation reaction of 2-arylisoquinolines. This protocol offers mild reaction conditions, high atom economy, and remarkable yield with excellent stereoselectivity, delivering enantioenriched axially chiral silane platform molecules with facile convertibility. The success of this unprecedented transformation relies on a novel chiral PSiSi-ligand, which facilitates the intermolecular C-H silylation process with perfect chem-, regio-, and stereo-control via a multi-coordinated silyl iridium complex.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yulei Wang, Joao C. A. Oliveira, Zhipeng Lin, Lutz Ackermann
Summary: The study introduces the first electrochemical metal-catalyzed [5+2] cycloadditions, assembling seven-membered benzoxepine skeletons with a high substrate scope and efficiency. The mechanistic studies support a rhodium(III/I) regime involving a benzoxepine-coordinated rhodium(I) sandwich complex as the catalyst resting state.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Julien Roger, Charline Sire, Anthonia Tsivery, Helene Cattey, Jean-Cyrille Hierso
Summary: We report a simple and efficient method for the peri-C-H functionalization of polyarylphosphines using aryl triflates as electrophile coupling partners. A [Rh(III)Cl2Cp*]2 precatalyst is employed to achieve high yields of polyarylated phosphines. This method is tolerant of various substituents and bulky polyaromatic triflate substrates.
SYNTHESIS-STUTTGART
(2023)
Article
Biochemistry & Molecular Biology
Ziwei Huang, Qiao Lin, Jiefang Li, Shanshan Xu, Shaohuan Lv, Feng Xie, Jun Wang, Bin Li
Summary: In this study, a regio- and stereoselective ruthenium-catalyzed dehydrogenative intermolecular silylation was developed for the synthesis of (E)-alkenyl silyl-ether derivatives and silyl-ether heterocycles with good functional group tolerance.
Article
Chemistry, Multidisciplinary
Gabriel Durin, Albane Fontaine, Jean-Claude Berthet, Emmanuel Nicolas, Pierre Thuery, Thibault Cantat
Summary: The metal-free catalytic hydrogenolysis of silyl triflates and halides to hydrosilanes is achieved using arylborane Lewis acids as catalysts. The catalyst acts as a Frustrated Lewis Pair and is able to split H-2 and generate a boron hydride intermediate capable of reducing (pseudo)halosilanes. This metal-free organocatalytic system competes with metal-based catalysts and enables the formation of a variety of hydrosilanes at room temperature in high yields under low hydrogen pressure.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Muhua Wang, Linghua Zhang, Xi Chen, Xinying Zhang, Xuesen Fan
Summary: A novel synthesis of pyrazolidinone fused 1,3-benzooxazepine derivatives via a formal [4 + 3] annulation reaction of 1-phenylpyrazolidinones with diazonaphthalen-2(1H)-ones is presented. The mechanism involves an unprecedented reaction mode of 1-phenylpyrazolidinone, featuring cascade C-alkylation/C-annulation through C(sp(2))-H/C(sp(3))-H bond cleavage. Compared with literature methods, this protocol offers advantages such as easily accessible starting materials, structurally complex and biologically attractive products, a unique mechanistic pathway, and excellent chemo/regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Nanoscience & Nanotechnology
Zahra Pournorouz, Amirhossein Mostafavi, Aditya Pinto, Apparao Bokka, Junha Jeon, Donghyun Shin
NANOSCALE RESEARCH LETTERS
(2017)
Article
Chemistry, Organic
Apparao Bokka, James X. Mao, John Hartung, Steven R. Martinez, Justin A. Simanis, Kwangho Nam, Junha Jeon, Xiaoqiang Shen
Article
Chemistry, Physical
Thirupataiah Avullala, Parham Asgari, Yuanda Hua, Apparao Bokka, Shawn G. Ridlen, Kyungsuk Yum, H. V. Rasika Dias, Junha Jeon
Article
Chemistry, Multidisciplinary
Hakan Arslan, Amirali Nojoomi, Junha Jeon, Kyungsuk Yum
Article
Engineering, Environmental
Akshay Chandrashekar Parenky, Naomi Gevaerd de Souza, Hiep H. Nguyen, Junha Jeon, Hyeok Choi
JOURNAL OF ENVIRONMENTAL ENGINEERING
(2020)
Article
Chemistry, Analytical
Matin Torabinia, Udaya Sree Dakarapu, Parham Asgari, Junha Jeon, Hyejin Moon
Summary: This study demonstrates the use of an electrowetting-on-dielectric digital microfluidic device as an efficient in-line work-up tool for organic chemical synthesis reactions, showing the device's capability to optimize operational parameters and adapt to various processes.
SENSORS AND ACTUATORS B-CHEMICAL
(2021)
Article
Chemistry, Analytical
Changling Qiu, Parham Asgari, X. James Mao, Junha Jeon, Kevin A. Schug
Summary: Organosilanes are important compounds used in industrial and personal care products, and their synthesis requires careful evaluation. This study successfully analyzed Si-containing compounds using gas chromatography with VUV detection, demonstrating the potential of VUV in the analysis of organosilanes' absorption spectra.
Article
Chemistry, Physical
Thirupataiah Avullala, Hiep H. Nguyen, Udaya Sree Dakarapu, Parham Asgari, Yuanda Hua, Junha Jeon
Summary: In this study, a method for oxidative C-C activation and silylation of cyclopropanols was reported. By consecutive iridium and rhodium catalysis, α,β-difunctionalized ketones were synthesized with high selectivity.
Article
Engineering, Environmental
Akshay Chandrashekar Parenky, Naomi Gevaerd de Souza, Parham Asgari, Junha Jeon, Mallikarjuna N. Nadagouda, Hyeok Choi
ENVIRONMENTAL ENGINEERING SCIENCE
(2020)
Article
Biochemical Research Methods
Matin Torabinia, Parham Asgari, Udaya Sree Dakarapu, Junha Jeon, Hyejin Moon
Article
Chemistry, Physical
Parham Asgari, Yuanda Hua, Apparao Bokka, Chanachon Thiamsiri, Watcharapon Prasitwatcharakorn, Ashif Karedath, Xin Chen, Sinjinee Sardar, Kyungsuk Yum, Gyu Leem, Brad S. Pierce, Kwangho Nam, Jiali Gao, Junha Jeon
Article
Nanoscience & Nanotechnology
Kwan Lee, Amirali Nojoomi, Junha Jeon, Chang Young Lee, Kyungsuk Yum
ACS APPLIED NANO MATERIALS
(2018)
Meeting Abstract
Chemistry, Multidisciplinary
Parham Asgari, Yuanda Hua, Thirupataiah Avullala, Junha Jeon
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2017)
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.
