Article
Chemistry, Multidisciplinary
Christian D. -T. Nielsen, Filip G. Zivkovic, Franziska Schoenebeck
Summary: The study reported a synthetic method for N-trifluoromethyl alkynamides and found that this synthetic compound can serve as a platform to unlock access to other valuable derivatives.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Muhammad Aliyu Idris, Kwang Ho Song, Sunwoo Lee
Summary: This study presents a new method for synthesizing acyl fluorides under environmentally friendly conditions without the need for transition-metal catalysts or additives. The methodology demonstrates good functional group tolerance towards various groups.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Chen Zhu, Serik Zhumagazy, Huifeng Yue, Magnus Rueping
Summary: This study presents a novel method for deoxygenated fluorination of readily available carboxylic acids, resulting in the synthesis of a series of acyl fluorides. Scale-up reactions and sequential cross-couplings successfully demonstrated the feasibility and practicality of this fluorination protocol.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Lei Liu, Long-Yu Ran, Yucheng Gu, Cheng-Pan Zhang
Summary: Tetramethylammonium trifluoromethylselenate has been confirmed as an excellent precursor for selenofluorophosgene, allowing for the preparation of selenocarbamoyl fluorides, selenoureas, and heterocycles without the need for catalysts or additives. The reactions with different types of amines result in the formation of a variety of selenium-containing compounds.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Hsin-Ju Huang, Zijun Wu, Derek A. Pratt
Summary: Unsymmetric disulfides can be directly synthesized from carboxylic acids or trifluoroborate salts using N-perthiophthalimide derivatives (Harpp reagents) under photoredox catalysis. The Harpp reagents are reduced in situ to form perthiyl radicals, which then dimerize to tetrasulfides and ultimately lead to the formation of disulfides. Previous radical sulfurations with N-thiophthalimide reagents are likely to proceed through the formation of the corresponding disulfide as the sulfuration reagent.
Article
Chemistry, Multidisciplinary
Hengzhao Li, Mengqi Peng, Zemin Lai, Lei Ning, Xingyue Chen, Xiaoxu Zhang, Pengjie Wang, Roman Szostak, Michal Szostak, Jie An
Summary: A highly chemoselective reductive deuteration of acyl fluorides using SmI2 and D2O as the deuterium source has been developed, providing alpha,alpha-dideuterio alcohols with exceptional levels of deuterium incorporation. This method introduces acyl fluorides as attractive radical precursors for the generation of reactive acyl-type fluoride ketyls, which should have widespread application in synthetic strategies involving single electron transfer processes.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Giulio Bresciani, Stefano Zacchini, Luca Famlonga, Guido Pampaloni, Fabio Marchetti
Summary: By carbonation of natural α-amino acids in water and subsequent cyclization with (2-bromo-1-arylethyl)dimethylsulfonium bromides, a series of 2-oxazolidinonyl derivatives were selectively produced without the need for purification. This method offers a more straightforward and efficient way to synthesize water-soluble compounds compared to previous approaches, showing potential for further reactions.
JOURNAL OF CO2 UTILIZATION
(2021)
Article
Chemistry, Organic
Xiu Wang, Fei Wang, Fengfeng Huang, Chuanfa Ni, Jinbo Hu
Summary: 3,3-Difluoro-1,2-diphenylcyclopropene (CpFluor), as a bench-stable fluorination reagent, has been developed for the deoxyfluorination of carboxylic acids to afford various acyl fluorides. This all-carbon-based fluorination reagent enables the efficient transformation of (hetero)aryl, alkyl, alkenyl, and alkynyl carboxylic acids to the corresponding acyl fluorides under neutral conditions, and features the synthesis of acyl fluorides with in-situ formed CpFluor and the one-pot amidation reaction of carboxylic acids via in-situ formed acyl fluorides.
Article
Chemistry, Applied
Jinhwan Park, Anattil Unnikrishnan Krishnapriya, Yeongmi Park, Minsuk Kim, Tyler W. Reidl, Rositha Kuniyil, Jongwoo Son
Summary: Dioxazolones and phosphines have been used in copper(I) catalysis to access N-acyl iminophosphoranes under simple thermal conditions. The synthetic utility of this method is demonstrated by its compatibility with a wide range of substrates and excellent atom-economy. Optimization experiments reveal that copper acts as a catalytic agent in the targeted transformation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Shang Gao, Jiaming Liu, Diego Troya, Ming Chen
Summary: This article reports a copper-catalyzed reaction that can synthesize ketone compounds with high enantioselectivity and excellent enantioenrichment, providing a valuable platform for further chemical transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Fanni Bede, Sandor Maho, Viktor Sandor, Gabor Mikle, Laszlo Kollar
Summary: The sterically highly unfavored position-7 of a steroidal skeleton was functionalized using conventional synthetic reactions and palladium-catalyzed aminocarbonylation. The synthesis involved the conversion of chenodeoxycholanic acid to 24-carboxamide, followed by oxidation of the 7-hydroxy group. The resulting 7-oxo functionality was then transformed into the corresponding iodoalkene using the Barton's method. A high-yielding aminocarbonylation of the 7-iodo-6-ene functionality was achieved using palladium-phosphine in situ catalysts and various amines as N-nucleophiles. The new 7-carboxamido compounds were obtained in good isolated yields through highly chemoselective reactions under relatively mild conditions.
Article
Chemistry, Organic
Yazhou Li, Yongkun Wang, Feifei Fang, Yu Zhang, Chunpu Li, Tao Yu, Qiangqiang Chen, Jiang Wang, Hong Liu
Summary: We have developed a method to construct five different types of N-acyl or N-sulfonyl aza-sulfur scaffolds using easily available (sulfon)amides and thiophthalimides. Our approach allows precise regulation of oxidants and features mild reaction conditions and simple operation, making it highly convenient for the late-stage diversification of various amide drugs, bioactive molecules, and peptides.
Article
Biochemistry & Molecular Biology
Theodora-Venera Apostol, Luminita Gabriela Marutescu, Constantin Draghici, Laura-Ileana Socea, Octavian Tudorel Olaru, George Mihai Nitulescu, Elena Mihaela Pahontu, Gabriel Saramet, Cristian Enache-Preoteasa, Stefania-Felicia Barbuceanu
Summary: New valine-derived compounds and 1,3-oxazole-based compounds were synthesized, showing promising antimicrobial and antibiofilm activities. While not all newly synthesized compounds exhibited significant biological activity, there is potential for future optimization by introducing various substituents on the phenyl moiety at position 5 of the 1,3-oxazole nucleus.
Article
Chemistry, Physical
Jinhang Dai, Qingya Cao, Ziting Du, Ronghe Yang, Delong Yang, Fukun Li, Xingxing Gu
Summary: This study investigates the catalytic reaction conditions for the oxidation of NMEA to N-acetylglycine, finding optimized conditions that result in high yields and conversion rates.
CATALYSIS COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Xue-Min Jia, Cheng Cheng, Ting Liu, Yong-Long Zhao, Bing Guo, Lei Tang, Yuan-Yong Yang
Summary: This study synthesized 39 N-acyl-2-aminopyrimidine derivatives and tested their inhibition efficacy on A. baumannii biofilm. Some of the analogues showed potential clinical significance and were demonstrated to be quorum sensing inhibitors.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Moritz E. Hansen, Samuel O. Yasmin, Susanne Wolfrum, Erick M. Carreira
Summary: The first total syntheses of tricyclic mutanobactins A and B, lipopeptides incorporating a thiazepanone, isolated from Streptococcus mutans, a member of the human oral microbiome, were reported. These natural products were rapidly delivered through a cascade of cyclization reactions using a solid-phase peptide synthesis (SPPS) based route. This versatile process was also used for a streamlined synthesis of mutanobactin D. Additionally, an independent synthesis of a truncated mutanobactin A analog, utilizing a novel thiazepanone amino acid building block, was provided.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Benedikt S. Schreib, Jacopo Margarini, Erick M. Carreira
Summary: The synthesis of picolinamides through Ritter reaction of 2-cyanopyridine with alcohols and alkenes is reported, and a range of additional heteroaryl nitriles successfully participate in the amidation reaction. The salient features of this reaction include operational simplicity and the use of inexpensive reagents. The synthetic utility of a camphene derived picolinamide is demonstrated through a palladium-catalyzed C-H arylation reaction.
Article
Chemistry, Multidisciplinary
Willi M. Amberg, Erick M. Carreira
Summary: This study presents the total synthesis of the complex molecule (+)-aberrarone using an Au-catalyzed-Sn-mediated cascade reaction, which efficiently closes four rings in the molecule. The method offers a stereoselective approach to synthesizing the natural product with a unique tetracyclic skeleton.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Viktoria C. Gerken, Erick M. Carreira
Summary: Graphitic carbon nitride (g-C3N4) is a photocatalyst used in the Giese reaction, showing excellent reusability and stability over five cycles with no changes in composition or morphology.
Article
Chemistry, Multidisciplinary
Nils Trapp, Michael Worle, Bernd Kuhn, Paul Gerber, Raffael Vorberg, Erick M. M. Carreira, Klaus Mueller
Summary: The molecular and crystal structures of 19 N-alkyl-substituted pipecolamide derivatives, including partial fluorination patterns, were presented. The different fluorination patterns in the N-alkyl group resulted in diastereomeric compounds with distinct crystal and molecular structures. The study also revealed an extraordinary conformational diversity in the various N-alkylpiperidine units, and provided insight into consistent conformational patterns and their modulation factors.
HELVETICA CHIMICA ACTA
(2023)
Article
Chemistry, Multidisciplinary
Supratim Ghosh, Avtar Changotra, David A. Petrone, Mayuko Isomura, Erick M. Carreira, Raghavan B. Sunoj
Summary: In this study, the mechanism of a chiral Ir-phosphoramidite-catalyzed asymmetric reductive deoxygenation reaction was investigated using density functional theory. It was found that Bi(OTf)3 promotes ionic and noncovalent interactions, which play a crucial role in nucleophile selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
David M. Fischer, Henry Lindner, Willi M. Amberg, Erick M. Carreira
Summary: Intermolecular cyclopropanation of mono-, di-, and trisubstituted olefins with alpha-bromo-beta-ketoesters and alpha-bromomalonates under organophotocatalysis is reported. The transformation exhibits broad functional group tolerance, producing highly substituted cyclopropanes. Mechanistic investigations, including Stern-Volmer quenching, quantum yield determination, and deuteration experiments, provide insights into the catalytic cycle.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Marlene Fadel, Erick M. Carreira
Summary: The first total synthesis of (+)-pedrolide, a tigliane-derived diterpenoid featuring an unprecedented 5-5-6-6-3 carbon skeleton, was achieved. A key step in the synthesis involved the construction of the bicyclo[2.2.1]heptane core via an intramolecular cyclopentadiene-Diels-Alder cycloaddition. A norbornadiene was used as a surrogate for cyclopentadiene, and the unmasking of the cyclopentadiene was achieved through a complex Diels-Alder reaction cascade. This synthesis also provided a novel approach to a densely functionalized carane in an efficient and enantioselective manner.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Editorial Material
Chemistry, Multidisciplinary
Erick M. Carreira
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Sven M. Papidocha, Hendrik H. Bulthaupt, Erick M. Carreira
Summary: The first total synthesis of heavily oxidized cassane-type diterpenoids, neocaesalpin A, AA, and nominal neocaesalpin K, was achieved using a redox-flexible platform as a key intermediate. The synthesis involved an intermolecular Diels-Alder reaction and a novel late-stage oxidation method for furfuryl acetate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Henry Lindner, Willi M. Amberg, Erick M. Carreira
Summary: In this study, unactivated olefins are converted into alkyl azides using bench-stable NaN3 in the presence of FeCl3·6H2O under blue-light irradiation. The reaction exhibits anti-Markovnikov selectivity and can be conducted under mild ambient conditions in the presence of air and moisture.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Hendrik H. Bulthaupt, Fabian Glatz, Sven M. Papidocha, Chunyan Wu, Shawn Teh, Susanne Wolfrum, Lucia Balazova, Christian Wolfrum, Erick M. Carreira
Summary: This study reports the synthesis and enantioselectivity of a series of compounds, and reveals the stimulating effect of one of the compounds on the respiration of brown adipocytes, which has potential applications in obesity treatment.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
David M. Fischer, Manuel Freis, Willi M. Amberg, Henry Lindner, Erick M. Carreira
Summary: We have developed a method for difunctionalization of unactivated, terminal olefins using intermolecular addition of alpha-bromoketones, -esters, and -nitriles followed by formation of 4- to 6-membered heterocycles with pendant nucleophiles. The reaction can be conducted with alcohols, acids, and sulfonamides as nucleophiles, yielding products with 1,4 functional group relationships that can be further manipulated. The reaction employs a benzothiazinoquinoxaline organophotoredox catalyst at a low catalyst loading and is tolerant to air and moisture.
Article
Chemistry, Multidisciplinary
Monica Guberman, Miroslav Kosar, Anahid Omran, Erick M. Carreira, Marc Nazare, Uwe Grether
Summary: Labeled chemical probes are crucial for the development and commercialization of drugs. They play a significant role in various research phases and provide valuable tools for specific application needs. The reverse-design approach enables the generation of high-quality probes based on previously optimized small molecules, fostering collaborations between academia and industry.
Article
Chemistry, Multidisciplinary
David M. Fischer, Moritz Balkenhohl, Erick M. Carreira
Summary: The cycloisomerization of beta-, gamma-, and delta-unsaturated N-acyl sulfonamides to N-sulfonyl lactams and imidates using a CoIII(salen) catalyst with t-BuOOH or air as the oxidant is reported in this study. The method exhibits good functional group tolerance and provides a new class of cyclic building blocks. The strong solvent dependence of the transformation and the synthetic versatility of the N-sulfonyl imidate product class are highlighted.