Article
Chemistry, Organic
Kailas V. Preeti, Kailas V. Kallurkar, Prathama S. Mainkar, Raju Adepu, Srivari Chandrasekhar
Summary: A concise route for the synthesis of dihydrobenzo-[j]-phenanthridinones has been developed using an aryne annulation strategy under metal-free reaction conditions. The reaction involves multiple C-C and C-N bond cleavages/formations through Diels-Alder reaction, aromatization-driven C-N bond cleavage, and amide formation.
Review
Biochemistry & Molecular Biology
Pau Nadal Rodriguez, Ouldouz Ghashghaei, Andrea Bagan, Carmen Escolano, Rodolfo Lavilla
Summary: This article introduces a synthetic approach for dealing with the structural complexity of molecules, which offers advantages in terms of synthetic economy and the preparation of larger amounts of drugs. The article summarizes the scientific methodology and main results of the research, provides a general appraisal of the current situation, and offers perspectives on future research directions.
Review
Chemistry, Medicinal
Amol A. Nagargoje, Mubarak H. Shaikh, Bapurao B. Shingate
Summary: Curcumin, an important phytochemical found in Asian countries, has garnered interest from medicinal chemists worldwide for its potential use in the synthesis of curcumin-based heterocycles via multicomponent reactions (MCRs). This review focuses on the MCRs involving curcuminoids as reactants to synthesize curcumin-based heterocycles and discusses the pharmacological activities of these compounds. The review primarily examines research published in the last decade.
ARCHIV DER PHARMAZIE
(2023)
Article
Chemistry, Organic
Shubhendu S. Karandikar, Bryan E. Metze, Riley A. Roberts, David R. Stuart
Summary: In this study, a one-pot reaction involving diaryliodonium and aryne intermediates is used to substitute the boron group and ortho-hydrogen atom in arylboron compounds. The method demonstrates the versatility of arylboron reagents and arynophiles, and is applied to the formal synthesis of a potential drug candidate.
Article
Biochemistry & Molecular Biology
Rahul Yadav, Tasneem Parvin, Anoop Kumar Panday, Lokman H. Choudhury
Summary: This method involves a rapid catalyst-free three-component reaction in ethanol medium under reflux conditions to access styryl-linked dihydropyridines fused with naphthoquinone and pyrazole. It is notable for its catalyst-free conditions, short reaction time, high product yields, easy purification process, formation of three new bonds, and products with four different bioactive moieties.
MOLECULAR DIVERSITY
(2021)
Article
Chemistry, Multidisciplinary
Philip J. Chevis, Chi Bong Eric Chao, Christopher Richardson, Christopher Hyland, Richmond Lee, Stephen G. Pyne
Summary: The crotylation reactions of chiral α-F, α-OBz and α-OH aldehydes were carried out under Petasis-borono-Mannich conditions using (E)- or (Z)-crotylboronates and primary amines. The reactions resulted in γ-addition products with high diastereoselectivity and enantioselectivity. The stereochemical outcomes of the reactions could be explained using transition state models and were supported by DFT calculations. Representative products were transformed into highly functionalized 1,2,3,6-tetrahydropyridines and 3H-oxazolo[3,4-a]pyridine-3-ones, which are valuable scaffolds in synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Daniel Lee, Sean P. Ross, Xiao Xiao, Thomas R. Hoye
Summary: Polycyclic, highly fused, and highly conjugated aromatic organic compounds have been of interest to chemists since the discovery of naphthalene in 1821. In recent decades, these compounds have attracted increasing attention due to their structures, properties, and wide-ranging practical applications. The development of new methods and strategies for synthesizing polycyclic aromatic compounds with new structural motifs is important in order to create novel molecular topologies.
Article
Chemistry, Organic
Xinkan Yang, Gavin Chit Tsui
Summary: Organic molecules with the trifluoromethyl group are important in pharmaceuticals, agrochemicals, and materials. New trifluoromethylation methods need to address efficiency, selectivity, and the source of CF3. Fluoroform has emerged as an attractive source of CF3 and can be used to efficiently and selectively synthesize trifluoromethylated compounds.
Article
Chemistry, Multidisciplinary
Maximilian Scheruebl, Constantin G. Daniliuc, Armido Studer
Summary: The article introduces the application of arynes as radical acceptors, showing how the stable radical TEMPO can react with different ortho-substituted benzynes to generate aryl radicals for subsequent cyclizations, eventually being trapped by TEMPO. This method provides a novel approach for the convenient synthesis of various dihydrobenzofurans, oxindoles, and sultones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ouldouz Ghashghaei, Pau Nadal Rodriguez, Rodolfo Lavilla
Summary: This Account summarizes the research of the group on multicomponent reactions using fundamental heterocycles as substrates. Mechanistic considerations are used to propose new processes and rationalize results. The potential biomedical applications of the resulting adducts are also explored, leading to interesting discoveries.
Article
Chemistry, Multidisciplinary
Eva Kran, Christian Muck-Lichtenfeld, Constantin G. Daniliuc, Armido Studer
Summary: In this study, the reaction of in situ generated arynes with stannylated imines to provide ortho-stannyl-aniline derivatives was reported, with good yields and regioselectivities. The product anilines are valuable starting materials for follow-up chemistry due to the rich chemistry offered by the trimethylstannyl moiety.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Hana Nakajima, Yuki Hazama, Yuki Sakata, Keisuke Uchida, Takamitsu Hosoya, Suguru Yoshida
Summary: This method efficiently synthesizes a diverse range of diaryl sulfides by utilizing aryne intermediates generated from o-iodoaryl triflates and methylthio-substituted o-silylaryl triflates.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Tsukasa Tawatari, Ritsuki Kato, Riku Kudo, Kiyosei Takasu, Hiroshi Takikawa
Summary: In this study, we report on the intramolecular (3+2) cycloaddition reactions between ynamides and benzyne. These reactions involve the formation of two bonds and are facilitated by using benzyne precursors containing a chlorosilyl group. The intermediate indolium ylide in these reactions exhibits both nucleophilic and electrophilic properties at its C2 atom.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Divanshu Gupta, Holger F. Bettinger
Summary: Ortho-benzyne and 1,2-azaborinine are structurally related. Computational studies reveal that the (2 + 2) and (2 + 4) cycloaddition reactions of 1,2-azaborinine with various organic pi systems are highly exothermic and involve the formation of Lewis acid-base complexes. The interaction between the pi bond of the substrates and the empty p orbital of the boron atom in these complexes is remarkably strong, leading to two-step mechanisms for the reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Alexandre Desaintjean, Fanny Danton, Paul Knochel
Summary: A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents can be prepared in toluene within 10 to 120 minutes between -78 degrees C and 25 degrees C via an I/Mg- or Br/Mg-exchange reaction using specific reagents. These exchange reactions tolerate highly sensitive functional groups and enable the synthesis of various functionalized compounds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Applied
Hamid Azizollahi, Marta Perez-Gomez, Vaibhav P. Mehta, Jose-Antonio Garcia-Lopez
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Applied
Hamid Azizollahi, Hossein Eshghi, Jose-Antonio Garcia-Lopez
Summary: This paper introduces a green magnetic efficient palladium catalyst for Suzuki-Miyaura coupling reactions and the synthesis of pyrimido[4,5-b]indoles, with high yield and fast reaction rate. The catalyst can be easily recovered using an external magnet device and recycled multiple times without significant loss of catalytic activity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Itziar Penafiel, Robert A. W. Dryfe, Nicholas J. Turner, Michael F. Greaney
Summary: The integration of electro and bio-catalysis offers new ways of making molecules under very mild, environmentally benign conditions. The combined process offers a new approach to amine alkylation with native alcohols, a key bond formation in the chemical economy that is currently achieved via precious metal-catalyzed hydrogen-borrowing technologies.
Review
Biochemistry & Molecular Biology
Hamid Azizollahi, Jose-Antonio Garcia-Lopez
Article
Chemistry, Inorganic & Nuclear
Jose-Antonio Garcia-Lopez, Maria-Jose Oliva-Madrid, Delia Bautista, Jose Vicente, Isabel Saura-Llamas
Summary: This study involves the synthesis of metallacycles by inserting alkynes into Pd-C bonds of ortho-metalated homoveratrylamine and phentermine, which further react with alkenes to form mononuclear complexes. Depending on the type of olefin used, different types of Pd(II) complexes are obtained. When terminal alkenes are used, anti/syn eta(3)-allyl Pd(II) complexes are formed; whereas using 2-norbornene leads to the formation of norbornyl palladium(II) complexes with a 10-membered ring structure.
Article
Chemistry, Physical
Elliott J. Craven, Jonathan Latham, Sarah A. Shepherd, Imtiaz Khan, Alba Diaz-Rodriguez, Michael F. Greaney, Jason Micklefield
Summary: New chemo- and biocatalytic methodologies are crucial for the sustainable synthesis of essential molecules in the future. Transition metal catalysis allows for late-stage C-H functionalization of complex molecular scaffolds, while enzymes provide exquisite regioselectivity but access to fewer functionalities compared to more divergent chemocatalysis.
Article
Chemistry, Multidisciplinary
David M. Whalley, Jayasree Seayad, Michael F. Greaney
Summary: The ring-opening of 3-aminocyclobutanone oximes leads to the formation of primary alkyl radicals, enabling a novel strain-release, desulfonylative radical Truce-Smiles rearrangement process, which allows for the divergent synthesis of valuable 1,3 diamines and unnatural beta-amino acids. The protocol is characterized by mild conditions and a wide range of migrating species, facilitating the modular assembly of sp(3)-aryls under transition metal-free, room-temperature conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Inorganic & Nuclear
Jose-Antonio Garcia-Lopez, Isabel Saura-Llamas
Summary: This manuscript reviews different approaches for the synthesis of C,C-palladacycles and their relevance in catalytic transformations. The strategies include elemental steps like oxidative addition of C-C bonds and more complex processes involving multiple Pd chemistry steps. Furthermore, it highlights synthetic methodologies based on Pd catalysis with C,C-palladacyclic intermediates.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Terence Wu, Matthew R. Tatton, Michael F. Greaney
Summary: This study demonstrates that pyridinium ions can undergo NHC addition and intramolecular C-C bond formation through a deoxy-Breslow intermediate, presenting a new pathway for catalytic reactions of non-aldehyde substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Thomas Sephton, Jonathan M. Large, Sam Butterworth, Michael F. Greaney
Summary: Diarylamines can be synthesized directly from sulfinamides through a new rearrangement sequence. This transition metal-free transformation offers an easy access to highly sterically hindered diarylamines, which cannot be obtained by traditional SNAr chemistry. The distinct reactivity of the sulfinamide group in Smiles rearrangements compared to the more common sulfonamides is highlighted.
Review
Chemistry, Organic
David M. Whalley, Michael F. Greaney
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Inorganic & Nuclear
Marta Perez-Gomez, Piedad Herrera-Ramirez, Delia Bautista, Isabel Saura-Llamas, Jose-Antonio Garcia-Lopez
Summary: A Pd-catalyzed synthesis method for heterocycles with a tetrasubstituted alkene fragment is reported. The method involves the intramolecular carbopalladation of tethered alkynes combined with an alkylation step produced by the C-C cleavage of cyclobutanol derivatives. An alkenyl-Pd(II) intermediate was isolated and characterized by X-ray diffraction studies. It was found that the nature of the tethering alkynyl chain affects the E/Z stereochemistry of the alkenyl fragment in the functionalized heterocycles.
Editorial Material
Chemistry, Multidisciplinary
Terence Wu, Michael F. Greaney
Summary: Diaryliodonium salts are versatile arylating agents, but they generally have poor atom economy. In this article, Olofsson and his colleagues describe a novel chemoselective SNAr reaction that incorporates the iodoarene component in a cascade arylation, achieving excellent atom economy.
Article
Chemistry, Multidisciplinary
David M. Whalley, Hung A. Duong, Michael F. Greaney
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Arunachalam Sagadevan, Anastasios Charitou, Fen Wang, Maria Ivanova, Martin Vuagnat, Michael F. Greaney
