Article
Chemistry, Multidisciplinary
Shashank Shandilya, Manash Protim Gogoi, Shubham Dutta, Akhila K. Sahoo
Summary: Ynamide, a unique species with inherited polarization of nitrogen lone pair electron to triple bond, has been widely used for the development of novel synthetic methods and the construction of unusual N-bearing heterocycles. This review provides an overall scenic view into the gold catalyzed transformation of ynamides, including their reactivity towards various transfer reagents and carbon nucleophiles.
Article
Chemistry, Applied
Ban Wang, Gavin E. Mccabe, Mitchell J. Parrish, Jujhar Singh, Matthias Zeller, Yongming Deng
Summary: A photoinduced selective hydroamination reaction of ynamides with nitrogen heteroaromatic nucleophiles has been developed using an organocatalytic photoredox system. This method allows for the direct construction of a diverse range of (Z)-alpha-azole enamides from ynamides and pyrazoles, triazoles, benzotriazoles, indazoles, and tetrazoles, providing a photocatalytic synthetic route to heterocyclic motifs commonly found in medicinal agents.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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
Joshua D. Priest, Louise Male, Paul W. Davies
Summary: This study demonstrates high diastereoselectivity in the synthesis of allyl sulfonium ylides through a gold-catalyzed multicomponent route. Modifying the substrate structure, N-phenyl methanesulfonamide derived ynamides are found to be the most effective precursors.
Article
Chemistry, Physical
Kaili Yan, Hyuna Kwon, Morgan Huddleston, De-en Jiang, Yujie Sun
Summary: Electrocatalytic biomass valorization has gained increasing interest, but reports on pyridine-containing chemicals from biomass upgrading are rare. In this study, we describe an electrochemical synthesis of 3-pyridinol from biomass-derived furfurylamine, achieving a 97% yield. The use of a Br-/Br+ redox cycle and strong acidic conditions was crucial for driving the final dehydration step. Control experiments and computational investigations were conducted to elucidate the key mechanistic steps of the one-pot conversion of furfurylamine to 3-pyridinol.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Applied
Fernando Martinez-Lara, Anisley Suarez, Noelia Velasco, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The gold-catalyzed transformation of propargylic glycols with thiols results in the formation of alpha-indol-3-yl alpha-((Z)-2-thioalkenyl) ketones through a complex but selective reaction mechanism. This sequence involves regioselective thiolation of indolyl diols followed by the attack of sulfur on the activated alkyne, rather than the indole. The final compounds are obtained in high yields from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide, and thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Miguel A. Munoz-Torres, Fernando Martinez-Lara, Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The combination of organolithium chemistry with gold catalysis offers a new synthetic strategy for accessing polysubstituted indoles and carbazoles. This method utilizes ketopyrroles as starting materials and involves a series of reactions to selectively synthesize the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Teng Yuan, Kelton Radefeld, Chuan Shan, Carter Wegner, Erin Nichols, Xiaohan Ye, Qi Tang, Lukasz Wojtas, Xiaodong Shi
Summary: Here, we have reported an intermolecular asymmetric hydrative aldol reaction by using a vinyl-gold intermediate under ambient conditions. This reaction provides a base-free approach to β-hydroxy amides with high efficiency, yielding up to 95% and with over 50 examples. The use of vinyl gold intermediate as a reactive nucleophile and Fe(acac)(3) as a critical co-catalyst prevents undesired protodeauration, allowing the transformation to proceed under mild conditions with excellent functional group tolerance and stereoselectivity (>20:1 d.r. and up to 99% ee).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Changliu Wang, Chunyu Han, Jinhua Yang, Zhenjia Zhang, Yongli Zhao, Junfeng Zhao
Summary: This study describes an environmentally friendly synthesis of thioamides and primary thioamides using a simple and mild reaction conditions and readily available NaSH as the sulfur source. The reaction can tolerate a wide range of functional groups and maintains the stereochemical integrity of alpha-chiral monothiocarboxylic acids, offering a racemization-free strategy for peptide C-terminal modification. Additionally, this method can be used to prepare thioamide-modified drugs and backbone thiazolyl modified peptides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
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, Multidisciplinary
Andreas S. S. Kalogirou, Andreas Kourtellaris, Panayiotis A. A. Koutentis
Summary: The oxidation of various non-S-oxidized 4H-1,2,6-thiadiazines using different reagents was studied. PIFA was found to be the most efficient reagent for the oxidation of 3,5-diamino-4H-1,2,6-thiadiazin-4-ones to sulfones. Single crystal structures of several compounds were also reported.
Article
Chemistry, Applied
Robin Heckershoff, Lukas Eberle, Garrett May, Petra Kraemer, Frank Rominger, Matthias Rudolph, A. Stephen K. Hashmi
Summary: The recently developed gold-catalyzed synthesis of indolo[1,2-a]quinolines has been successfully expanded to bidirectional approaches, allowing access to two heptacyclic structural motifs. New nitrogen-containing heptacycles, benzobispyrrolo[1,2-a]quinolines, were synthesized using alkynylated benzodipyrrole derivatives. The study revealed important structure-effect relationships between solid-state structures and photophysical properties.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Jenna L. Miller, Krishnan Damodaran, Paul E. Floreancig
Summary: This manuscript describes a protocol to form acyliminium ions and related species through hydride abstractions of easily accessible allylic carbamates, amides, and sulfonamides. These intermediates are used in the synthesis of nitrogen-containing heterocycles, demonstrating high levels of stereocontrol. Areas of investigation include oxidation efficiency, geometry of intermediate iminium ions, substrate stereocenter impact on stereocontrol, and transition state geometry.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Yanling Zhan, Yifan Li, Jinwen Tong, Ping Liu, Peipei Sun
Summary: A new method for regioselective C-H cyanation of quinoxalin-2(1H)-ones was developed using a nucleophilic cyano source TMSCN under electrochemical oxidative conditions. The process allowed for the synthesis of C3 cyanated quinoxalin-2(1H)-ones in moderate to excellent yields without the need for transition-metal catalysts and organic hydroperoxides.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yanyang He, Xiaowen Qin, Xinxu He, Xiao-Feng Wu, Zhiping Yin
Summary: An efficient intramolecular halo-amination reaction of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This method allows the construction of a wide range of halogenated N-heterocycles at moderate to good yields, including three-, five-, and six-membered N-heterocycles, without the need for external oxidants and strong bases, representing an environmentally benign approach.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Holly V. Adcock, Elli Chatzopoulou, Paul W. Davies
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Applied
Andrew D. Gillie, Raju Jannapu Reddy, Paul W. Davies
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Multidisciplinary
Fernando Sanchez-Cantalejo, Joshua D. Priest, Paul W. Davies
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Organic
Yiming Zhao, Matthew G. Wakeling, Fernanda Meloni, Tze Jing Sum, Huy Van Nguyen, Benjamin R. Buckley, Paul W. Davies, John S. Fossey
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Applied
Elsa M. Arce, Scott G. Lamont, Paul W. Davies
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Paige A. Rist, Richard S. Grainger, Paul W. Davies
Summary: Selective C3-alkylation of benzothiophenes was achieved through a gold-catalyzed reaction, with the minor product being the C7-alkylated isomer. The reaction was successful with various alkyl and aryl alkynes and substituted or unsubstituted benzothiophenes, but the inhibitory effect of sulfoxide on the catalyst requires further investigation.
Article
Chemistry, Organic
Joshua D. Priest, Louise Male, Paul W. Davies
Summary: This study demonstrates high diastereoselectivity in the synthesis of allyl sulfonium ylides through a gold-catalyzed multicomponent route. Modifying the substrate structure, N-phenyl methanesulfonamide derived ynamides are found to be the most effective precursors.
Article
Chemistry, Organic
Parmjit Heer Kaur, Paul W. Davies
Summary: In this study, ynamides with tethered allyl sulfoxide undergo a gold-catalysed cycloisomerisation to yield tetrahydrothiophene-2-carboxamides and their benzo-fused analogues. The reactions are initiated by a formal 7-endo-dig cyclisation and can accommodate various substituents. Additionally, the use of N-allyl ynamides provides a pathway to novel spirocyclic epsilon-lactam structures.
Article
Chemistry, Physical
Peter E. Simm, Prakash Sekar, Jeffery Richardson, Paul W. Davies
Summary: The research demonstrates the controlled access to (3+2) annulation by Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers, resulting in the synthesis of sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety. This offers a new strategy for achieving varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes.
Article
Chemistry, Organic
Sifan Li, Yu Wang, Zibo Wu, Weiliang Shi, Yibo Lei, Paul W. Davies, Wei Shu
Summary: A radical triggered fragmentary cyclization cascade reaction is proposed to provide rapid access into [1,2]-annulated indoles. The mechanism involves radical addition, cyclization, aryl migration, and C-N bond cyclization sequence.
Article
Chemistry, Organic
Matthew P. Ball-Jones, Paul W. Davies
Article
Chemistry, Multidisciplinary
Raju Jannapu Reddy, Matthew P. Ball-Jones, Paul W. Davies
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Applied
Miguel Garzon, Elsa M. Arce, Raju Jannapu Reddy, Paul W. Davies
ADVANCED SYNTHESIS & CATALYSIS
(2017)
Article
Chemistry, Multidisciplinary
Matthew J. Barrett, Ghulam F. Khan, Paul W. Davies, Richard S. Grainger
CHEMICAL COMMUNICATIONS
(2017)
