Article
Multidisciplinary Sciences
Haofu Zhu, Pan-Pan Zhou, Yao Wang
Summary: This study reports a new method for activating aziridines by cooperative sulfur-arsenic bonding interactions, enabling their use in cycloaddition reactions with nonactivated alkenes.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Jinghui Tong, Renshi Luo, Liang Liu, Xiao Yang, Jianhua Liao
Summary: A visible light-induced transformation has been developed for the difluoroalkylation of unactivated alkenes using ethyl iododifluoroacetate. Depending on the choice of base, solvent, and loading of ethyl iododifluoroacetate, this reaction provides selective access to difluoroalkylated indole derivatives in good yields.
SYNTHESIS-STUTTGART
(2023)
Article
Multidisciplinary Sciences
Ting-Bi Hua, Cheng-Xiong Liu, Wei-Min Hu, Long Wang, Qing-Qing Yang
Summary: An efficient [4+1] annulation method has been developed for the synthesis of biologically interesting isoxazoline derivatives via in situ generation of nitrosoalkenes under mild basic reaction conditions, providing good to excellent yields.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Multidisciplinary
Dongshun Ni, Sai Hu, Xiangyu Tan, Yang Yu, Zhenghua Li, Li Deng
Summary: We propose a new method to synthesize complex polycyclic indoline compounds directly from readily available indoles and bicyclo[1.1.0]butanes (BCBs) using commercially available Lewis acids. The reaction involves nucleophilic addition of indoles to BCBs and intramolecular Mannich reaction, yielding rigid indoline-fused polycyclic structures. This new reaction allows the construction of various rigid indoline polycycles containing up to four contiguous quaternary carbon centers in a single step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Katarina Stefkova, Michael G. Guerzoni, Yara van Ingen, Emma Richards, Rebecca L. Melen
Summary: Here, a mild, transition-metal-free, highly diastereoselective Lewis acid catalyzed methodology for the synthesis of isoxazolidine-based diazo compounds from the reaction between vinyldiazo esters and nitrones is reported. Interestingly, the diastereoselectivity of the isoxazolidine products is found to be contrasting to previous metal-catalyzed reactions. Furthermore, the same catalyst can be used with enol diazo esters, leading to the formation of Mukaiyama-Mannich products. These diazo products can be further functionalized to generate benzo[b]azepine and pyrrolidinone derivatives.
Article
Chemistry, Organic
Kai Matsui, Kohei Toh, Manabu Hatano, Kazuaki Ishihara
Summary: A multiselective Diels-Alder reaction involving alpha-arylacroleins and cyclopentadiene has been developed using BBr3-assisted chiral BINOL-derived phosphoric acid catalysts. The chiral cavity of the in situ-formed acid-base cooperative catalysts plays a key role in controlling the exo- and enantioselectivity, particularly by suppressing the competitive hetero Diels-Alder reaction effectively.
Article
Chemistry, Multidisciplinary
Bradley K. Gall, Avery K. Smith, Eric M. Ferreira
Summary: A direct dearomative photocatalyzed (3+2) cycloaddition between indoles and vinyldiazo reagents is achieved using a novel oxidizing Cr-III photocatalyst. This transformation allows the synthesis of various fused indoline compounds, including densely functionalized ring systems, under base-free conditions. Experimental insights support a cycloaddition initiated by nucleophilic attack of the vinyldiazo species at C3 of the indole radical cation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Chiao-Ying Kuo, Jeh-Jeng Wang
Summary: A visible light-induced, atom-economical synthesis of furan-fused dihydroazepine derivatives under transition metal- and photocatalyst-free conditions is described. This efficient new method exhibits a broad scope and is environmentally benign and mild with metal-/photocatalyst and external additive-free conditions and moderate to good yields. The reaction mechanism has been studied, revealing that the transformation may proceed via non-radical pathways. The gram-scale reaction renders the approach practical and attractive, and the green chemistry metrics evaluation signifies that the process is green and cost-effective.
Article
Chemistry, Organic
Gang Shao, Chuang Niu, Hong-Wei Liu, Huan Yang, Jun-Shen Chen, Yang-Rong Yao, Shangfeng Yang, Guan-Wu Wang
Summary: The mechanochemical cascade reaction of [60]fullerene with various compounds has been investigated under solvent-free and ball-milling conditions. This method provides an efficient way to obtain [60]fullerene-fused cyclopentanes, with advantages of good substrate scope, short reaction time, and solvent-free and ambient reaction conditions. Additionally, these fullerene products have been successfully applied as efficient cathode interlayers in inverted planar perovskite solar cells.
Article
Chemistry, Organic
Zhe Meng, Xiaoyu Zhang, Min Shi
Summary: A novel fluoroalkylation and cycloisomerization cascade reaction of ene-VDCP with ethyl iododifluoroacetate or perfluoroalkyl iodide under visible-light irradiation is reported in this study, providing the desired fluorinated cyclization products in moderate to good yields and showing good functional group tolerance. Mechanistic investigations suggest the presence of a radical chain process in this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Kshitiz Verma, Manmath Mishra, Prabhat Kumar Maharana, Hemanga Bhattacharyya, Sharajit Saha, Tharmalingam Punniyamurthy
Summary: A Sc(III)-catalyzed domino C-C and C-N bond formation of N-sulfonyl aziridines with quinones has been achieved, leading to the synthesis of functionalized indolines at a moderate temperature. The key practical features of this study include the umpolung reactivity of aziridines, radical pathway, mild reaction conditions, substrate scope, and the coupling of drug molecules in a postsynthetic application.
Review
Chemistry, Multidisciplinary
Santosh Kumar Nanda, Rosy Mallik
Summary: Vicinal carboamination of alkynes is a reliable and efficient strategy for the synthesis of valuable and diverse amine derivatives. While transition-metal catalysis has been extensively studied, metal-free alternatives are also gaining attention. However, scattered reports have hindered further developments in this field. This review discusses different approaches and provides examples from the literature, giving insight into the mechanisms of these transformations.
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
Rei Tomifuji, Shunpei Murano, Takuya Kurahashi, Seijiro Matsubara
Summary: A methodology for the synthesis of cyclohexane scaffolds has been developed using an iron(III)-based Lewis acid catalyst. The unprecedented fully intermolecular [2+2+2] cycloaddition reaction of three alkenes was diastereoselective, producing multi-substituted cyclohexane products. The key role of the ionic species [FeBr2](+)[FeBr4](-) generated via disproportionation of FeBr3 was crucial for this catalysis, controlling the reaction path and suppressing undesired polymerization reactions.
Editorial Material
Chemistry, Multidisciplinary
Tuhin Patra, Thomas Wirth
Summary: This study investigates a novel oxidative cleavage method for alkenes, which involves the use of photosensitized nitroarenes to produce [3+2] cycloaddition products and convert them into carbonyl compounds. The method offers high site-selectivity and mild oxidation conditions, making it suitable for the synthesis of complex molecular structures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
James McNulty, David McLeod
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
James McNulty, David McLeod, Hilary A. Jenkins
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Multidisciplinary Sciences
David McLeod, James McNulty
ROYAL SOCIETY OPEN SCIENCE
(2016)
Article
Multidisciplinary Sciences
Sebastian Scheer, Suzanne Ackloo, Tiago S. Medina, Matthieu Schapira, Fengling Li, Jennifer A. Ward, Andrew M. Lewis, Jeffrey P. Northrop, Paul L. Richardson, H. Umit Kaniskan, Yudao Shen, Jing Liu, David Smil, David McLeod, Carlos A. Zepeda-Velazquez, Minkui Luo, Jian Jin, Dalia Barsyte-Lovejoy, Kilian V. M. Huber, Daniel D. De Carvalho, Masoud Vedadi, Colby Zaph, Peter J. Brown, Cheryl H. Arrowsmith
NATURE COMMUNICATIONS
(2019)
Review
Chemistry, Multidisciplinary
David McLeod, Mathias Kirk Thogersen, Nicolaj Inunnguaq Jessen, Karl Anker Jorgensen, Cooper S. Jamieson, Xiao-Song Xue, K. N. Houk, Fang Liu, Roald Hoffmann
ACCOUNTS OF CHEMICAL RESEARCH
(2019)
Article
Chemistry, Multidisciplinary
David McLeod, Alessio Cherubini-Celli, Nisanhi Sivasothirajah, Christina H. McCulley, Mette Louise Christensen, Karl Anker Jorgensen
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Multidisciplinary Sciences
Magdalena M. Szewczyk, Yoshinori Ishikawa, Shawna Organ, Nozomu Sakai, Fengling Li, Levon Halabelian, Suzanne Ackloo, Amber L. Couzens, Mohammad Eram, David Dilworth, Hideto Fukushi, Rachel Harding, Carlo C. dela Sena, Tsukasa Sugo, Kozo Hayashi, David McLeod, Carlos Zepeda, Ahmed Aman, Maria Sanchez-Osuna, Eric Bonneil, Shinji Takagi, Rima Al-Awar, Mike Tyers, Stephane Richard, Masayuki Takizawa, Anne-Claude Gingras, Cheryl H. Arrowsmith, Masoud Vedadi, Peter J. Brown, Hiroshi Nara, Dalia Barsyte-Lovejoy
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Giulio Bertuzzi, David McLeod, Lisa-Marie Mohr, Karl Anker Jorgensen
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Medicinal
David Smil, Jong Fu Wong, Eleanor P. Williams, Roslin J. Adamson, Alison Howarth, David A. McLeod, Ahmed Mamai, Soyoung Kim, Brian J. Wilson, Taira Kiyota, Ahmed Aman, Julie Owen, Gennady Poda, Kurumi Y. Horiuchi, Ekaterina Kuznetsova, Haiching Ma, J. Nicole Hamblin, Sue Cramp, Owen G. Roberts, Aled M. Edwards, David Uehling, Rima Al-awar, Alex N. Bullock, Jeff A. O'Meara, Methvin B. Isaac
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Physical
David McLeod, Joseph A. Izzo, Danny K. B. Jorgensen, Rune F. Lauridsen, Karl Anker Jorgensen
Article
Chemistry, Medicinal
Yudao Shen, Fengling Li, Magdalena M. Szewczyk, Levon Halabelian, Irene Chau, Mohammad S. Eram, Carlo Dela Sena, Kwang-Su Park, Fanye Meng, He Chen, Hong Zeng, Aiping Dong, Hong Wu, Viacheslav V. Trush, David McLeod, Carlos A. Zepeda-Velazquez, Robert M. Campbell, Mary M. Mader, Brian M. Watson, Matthieu Schapira, Cheryl H. Arrowsmith, Rima Al-Awar, Dalia Barsyte-Lovejoy, H. Umit Kaniskan, Peter J. Brown, Masoud Vedadi, Jian Jin
Summary: (R)-2 is a potent and highly selective inhibitor of PRMT6, binding to an induced allosteric pocket. It shows outstanding selectivity for PRMT6 over other methyltransferases and can be used as a valuable tool for further investigation of PRMT6 functions in health and disease.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yidong Liu, Joseph A. Izzo, David McLeod, Sebastijan Ricko, Esben B. Svenningsen, Thomas B. Poulsen, Karl Anker Jorgensen
Summary: Isobenzopyrylium ions are unexplored in asymmetric catalysis. A new organocatalytic method was developed to synthesize chiral tetrahydronaphthols with high yield, diastereoselectivity, and enantioselectivity. The bioactivity of these compounds was evaluated in cancer cells, showing unique profiles and morphological changes in some cases.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Nicolaj Inunnguaq Jessen, David McLeod, Karl Anker Jorgensen
Summary: This article discusses the classification and analysis of successful organocatalytic higher-order cycloadditions (HOCs). Aminocatalysis is the most commonly used activation strategy, and the lessons learned from it can contribute to the development of other organocatalytic strategies. The potential for continued growth of catalytic HOCs as a research field is demonstrated by sporadic examples.
Article
Chemistry, Multidisciplinary
David A. McLeod, Mathias Kirk Thogersen, Casper Larsen Barlose, Mette Louise Skipper, Erlaitz Basabe Obregon, Karl Anker Jorgensen
Summary: This study presents a novel enantioselective (8+3) cycloaddition reaction using a chiral bifunctional Bronsted base catalyst. The reaction leverages an anionic activation strategy and differs from typical Lewis-acid activation protocols. Experimental and computational results support the relevance of this reaction and its potential application in organic synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Johannes N. Lamhauge, David A. McLeod, Casper L. Barlose, Gwyndaf A. Oliver, Laura Viborg, Tobias Warburg, Karl Anker Jorgensen
Summary: This article reports a method for the synthesis of tropane derivatives using (5+2) cycloaddition reactions, with excellent stereo selectivity and yield. The mechanism and conditions of this reaction were determined through a series of experiments.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
