Article
Biochemistry & Molecular Biology
Zsolt Fulop, Peter Bana, Istvan Greiner, Janos eles
Summary: A new continuous-flow consecutive reduction method was developed for the C-N bond formation in the synthesis of the key intermediate of the antipsychotic drug cariprazine. The two-step procedure involved DIBAL-H mediated selective ester reduction and reductive amination using catalytic hydrogenation on 5% Pt/C. The connection of the optimized modules was achieved using at-line extraction to prevent precipitation of the aluminum salt byproducts.
Article
Chemistry, Multidisciplinary
Hao Wang, Hoimin Jung, Fangfang Song, Shiyang Zhu, Ziqian Bai, Danye Chen, Gang He, Sukbok Chang, Gong Chen
Summary: N-N linkages are important in natural compounds, and a nitrene-mediated intermolecular N-N coupling reaction using iridium or iron catalysis provides a simple and efficient method to synthesize various hydrazides from readily available carboxylic acid and amine precursors. Mechanistic studies show that the nitrogen atom of Ir acyl nitrene intermediates serves as a strong electrophile and can form N-N bonds with high efficiency and chemoselectivity with the assistance of Cl···HN hydrogen bonding.
Article
Chemistry, Organic
Keshu Yin, Mingjie Wei, Zhenguo Wang, Wenjun Luo, Le Li
Summary: A safer and more sustainable method for recycling organophosphorus compounds is achieved by reducing phosphine oxides without the use of highly reactive reductants. This is accomplished through an unusual intermolecular hydride transfer mediated by N,N,N',N'-tetramethylethylenediamine (TMEDA). Mechanistic studies reveal the role of TMEDA as a hydride donor and the P(V) halophosphonium salt as the hydride acceptor. This methodology provides a scalable and efficient protocol for mild reduction of phosphine oxides.
Article
Chemistry, Organic
Trevor G. Bolduc, Cayo Lee, William P. Chappell, Glenn M. Sammis
Summary: Thionyl fluoride (SOF2) is a promising reagent that has not been extensively studied for its synthetic applications. This research expands the scope of thionyl fluoride-mediated nucleophilic acyl substitutions and demonstrates its effectiveness in the synthesis of peptides, amides, esters, and thioesters. In addition, it shows that thionyl fluoride can be used as a mild reducing agent in one-pot reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Wei Liu, Zhen Lu, Shan Yuan, Xinglin Jiang, Mo Xian
Summary: N-N bonded compounds are a small but important group of natural products with diverse biological activities. Chemical synthesis is currently the main method for their synthesis, but safety and sustainability issues exist. Various biosynthetic mechanisms for NeN bonding exist in nature, but only a few NeN bond synthases have been reported, and biosynthesis of NeN bond-containing compounds faces difficulties. The newly discovered NeN bond synthase PAI2 shows improved catalytic activity and different enzymatic properties compared to the known enzyme KtzT, and it is capable of catalyzing the formation of CeN bonds in Pro.
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Tamanna Khandelia, Subhendu Ghosh, Bhisma K. Patel
Summary: A Cu(OTf)(2)-mediated regioselective dearomative aryl-hydroxylation across the C(sp(2))=N bond of 2-aryl quinoxalines and bis-Narylation of (benz)imidazoles were developed using aryl boronic acids. For the dearomative aryl-hydroxylation, the C-center should be electrophilic (ca. 0.08), the N-center nucleophilic (ca. -0.50), and the C(sp(2))=N bond polarized (delta e = 0.609).
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Chunyan Ge, Liang Wang, Fangzhi Hu, Zhanshuai Ding, Xinyao Li, Deshuai Xiao, Jiayi Wang, Shuai-Shuai Li
Summary: The three-component reaction of o-aminobenzaldehydes with 5-hydroxyindole and electron-rich arenes has been successfully achieved through HFIP-mediated cascade reaction at room temperature, providing a variety of 2-arylspiroindolenines carrying diverse functional groups with moderate to good yields. The derivatizations of the products have also been conducted to enhance the synthetic practicality of this protocol.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Mirdyul Das, Arantxa Rodriguez, Pui Kin Tony Lo, Wesley J. Moran
Summary: This study presents the preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates, allowing for a versatile range of substrates to be converted into substituted oxazolidinones ready for further transformations. Derivatization of the products at both ends is demonstrated in addition to a preliminary attempt at the enantioselective formation of an oxazolidinone using a chiral iodane.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Ling-Zhi Sun, Xuan Yang, Nan-Nan Li, Meng Li, Qin Ouyang, Jian-Bo Xie
Summary: A facile synthetic method for 4-aryl-4,5-dihydropyrrole-3-carboxylates has been developed using a rhodium-catalyzed ring expansion strategy. This method offers a novel mechanism and enables asymmetric catalytic synthesis with excellent diastereoselectivity, leading to the formation of substituted pyrrolidines.
Article
Chemistry, Organic
You-Qin Jiang, Yong-Hao Wang, Chen-Fan Zhou, Yun-Qian Zhang, Yong Ling, Yu Zhao, Gong-Qing Liu
Summary: This study reports the intermolecular carboselenenylation of easily accessible alkenes using diselenides and N-fluorobenzenesulfonimide (NFSI) under metal-free and mild conditions. Preliminary mechanistic studies demonstrate that the oxidation of diselenide by NFSI generates an active selenenyl cationic radical species through a single electron-transfer process, initiating the intermolecular carboselenenylation of olefins and forming key Se-C and C-C bonds. Under optimized conditions, a wide range of structurally and functionally diverse selenoether derivatives can be obtained with high yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ting-Kai Xiong, Xue-Qi Zhou, Min Zhang, Hai-Tao Tang, Ying-Ming Pan, Ying Liang
Summary: A novel electrocatalyzed three-component cascade reaction has been developed for synthesizing a series of new carbamate compounds efficiently and environmentally friendly. The reaction promotes the participation of carbon dioxide in the three-component reaction by electro-oxidation, and pharmacological activity studies demonstrate that the carbamate compounds have better activity than diamination by-products.
Article
Chemistry, Organic
Yingwei Wang, Mingrong Yang, Chichou Lao, Zhihong Jiang
Summary: We report a new and simple method for the synthesis of dl-2,3-diamide-1,4-diones. This method is highly efficient and environmentally friendly. Experimental results suggest that the substrate undergoes autoxidation followed by diastereoselective SN2 reaction.
Article
Chemistry, Multidisciplinary
Jiaoyu Wu, Linqiang Li, Mengtian Liu, Lu Bai, Xinjun Luan
Summary: A novel Pd-0-catalyzed [2+2+1] annulation was proposed for the rapid assembly of tricyclic indoles in a single-step transformation. Experimental results showed that large tert-butyl and benzyl groups were selectively cleaved via an S(N)1 pathway in the presence of smaller alkyl groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Bipin Kumar Behera, Archana Kumari Sahu, Ngangbam Renubala Devi, Anil K. Saikia
Summary: An efficient methodology has been developed for the synthesis of tetra- and pentasubstituted pyrroles with two carbonyl groups in the side chain. The protocol can be extended towards the synthesis of pyrrolo-[3,4-d]pyridazine.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jinhwan Park, Dongkyu Jang, Jihye An, Yeongmi Park, Hyeonwoong Bae, Minseok Kim, Joohyun Lee, Jongwoo Son
Summary: We highlight our recent studies on the synthesis of N-aryl amides using dioxazolones and boronic acids in the presence of copper(I) chloride under mild conditions. The developed reaction demonstrates wide range of functional group tolerances and the release of nontoxic carbon dioxide. Optimization screenings reveal the involvement of an N-acyl nitrene intermediate in this transformation.
Article
Chemistry, Organic
Ibrahim U. Kutama, Simon Jones
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
R. A. Bawa, F. -M. Gautier, H. Adams, A. J. H. M. Meijer, S. Jones
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Cell Biology
Anne L. Robertson, Nikolay V. Ogryzko, Katherine M. Henry, Catherine A. Loynes, Matthew J. Foulkes, Marco M. Meloni, Xingang Wang, Christopher Ford, Malcolm Jackson, Philip W. Ingham, Heather L. Wilson, Stuart N. Farrow, Roberto Solari, Roderick J. Flower, Simon Jones, Moira K. B. Whyte, Stephen A. Renshaw
DISEASE MODELS & MECHANISMS
(2016)
Article
Chemistry, Organic
Rebecca C. Collins, Martyn N. Paley, Gillian M. Tozer, Simon Jones
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Inorganic & Nuclear
Christopher J. A. Warner, Andrew T. Reeder, Simon Jones
TETRAHEDRON-ASYMMETRY
(2016)
Article
Radiology, Nuclear Medicine & Medical Imaging
Steven Reynolds, Stephen Metcalf, Edward J. Cochrane, Rebecca C. Collins, Simon Jones, Martyn N. J. Paley, Gillian M. Tozer
MAGNETIC RESONANCE IN MEDICINE
(2017)
Article
Chemistry, Organic
X. Li, A. T. Reeder, F. Torri, H. Adams, S. Jones
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Biology
Victoria A. Lund, Katarzyna Wacnik, Robert D. Turner, Bryony E. Cotterell, Christa G. Walther, Samuel J. Fenn, Fabian Grein, Adam J. M. Wollman, Mark C. Leake, Nicolas Olivier, Ashley Cadby, Stephane Mesnage, Simon Jones, Simon J. Foster
Article
Multidisciplinary Sciences
Matthew J. Foulkes, Katherine M. Henry, Julien Rougeot, Edward Hooper-Greenhill, Catherine A. Loynes, Phil Jeffrey, Angeleen Fleming, Caroline O. Savage, Annemarie H. Meijer, Simon Jones, Stephen A. Renshaw
SCIENTIFIC REPORTS
(2017)
Article
Chemistry, Organic
Alexander M. Fields, Simon Jones
Article
Chemistry, Organic
Christopher J. A. Warner, Sian S. Berry, Simon Jones
Article
Multidisciplinary Sciences
Matthew J. Foulkes, Faith H. Tolliday, Katherine M. Henry, Stephen A. Renshaw, Simon Jones
Article
Multidisciplinary Sciences
Peter Oatley, Joseph A. Kirk, Shuwen Ma, Simon Jones, Robert P. Fagan
SCIENTIFIC REPORTS
(2020)
Review
Chemistry, Organic
Sian S. Berry, Simon Jones
Summary: Chiral substituted pyrrolidines are key elements in biologically active molecules and are often synthesized using kinetic resolution methods to obtain enantiomerically pure compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel Ray Jenkinson, Ashley James Cadby, Simon Jones
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)