Article
Chemistry, Multidisciplinary
Xingxing Ma, Luo Li, Mengwei Tan, Zihao Zhong, Jinchao Liang, Puhui Li, Qiuling Song
Summary: Four migration reactions from alkynyl tetracoordinate boron species were reported, leading to the synthesis of tetrasubstituted alkenyl monohalides. This provides a new approach for the preparation of versatile tetrasubstituted olefins.
Article
Chemistry, Organic
Regina M. Oechsner, Ivo H. Lindenmaier, Ivana Fleischer
Summary: We present a nickel catalyzed C-S cross-coupling reaction of aryl and alkenyl triflates with alkyl thiols. By using an air-stable nickel precatalyst, various thioethers could be synthesized under mild reaction conditions within a short reaction time. The reaction demonstrated a broad substrate scope, including pharmaceutically relevant compounds.
Article
Chemistry, Multidisciplinary
Yuting Hu, Madison J. Wong, Bruce H. Lipshutz
Summary: A new technology has been reported that enables Negishi couplings to be conducted under sustainable and greener conditions using recyclable water as the medium and a low Pd loading. The results demonstrate the functional group tolerance associated with these couplings and the characterization of the reagent used.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Xiang Sun, Ke Zheng
Summary: An effective electrooxidation strategy for generating alkyl radicals from unactivated alkyl iodides via an electrochemical halogen-atom transfer process under mild conditions is reported here.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Fuyang Yue, Jianyang Dong, Yuxiu Liu, Qingmin Wang
Summary: Here we describe a mild and general protocol for the alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones under visible light. The method allows for efficient functionalization of sulfones with a wide range of alkyl groups and can be scaled to gram levels. Its excellent tolerance to functional groups and mild conditions make it suitable for late-stage functionalization of natural products and drug molecules.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Dmitrii Kalinin, Trond Ulven
Summary: A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)-aryl ketones is described. The protocol utilizes the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure to facilitate the carbonylative coupling between various C-(sp3)-hybridized organozinc reagents and a wide range of aryl iodides, including substrates with aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chao-Shen Zhang, Bei-Bei Zhang, Liang Zhong, Xiang-Yu Chen, Zhi-Xiang Wang
Summary: A DFT study was conducted to investigate the asymmetric alkyl-alkyl bond formation through nickel-catalysed reductive coupling. The study found that the Ni(ii) precursor can be easily activated/reduced to Ni(0) species under the reductive experimental conditions, which then serves as an active species in the Ni(0)/Ni(ii) catalytic cycle. Alternatively, a Ni(i)/Ni(ii)/Ni(iii) catalytic cycle starting with a Ni(i) species such as Ni(i)-Br was proposed. The presence of K3PO4 greatly facilitates the hydrosilane hydride transfer and olefin reduction. The origins of enantioconvergence and enantioselectivity control were discussed based on the two catalytic cycles.
Article
Chemistry, Organic
Yanling Zhang, Zhiguo Zhang, Yuanyuan Hu, Yunkui Liu, Hongwei Jin, Bingwei Zhou
Summary: We have described a nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides. Aryl/alkenyl iodines and bromides were found to be competent electrophiles that reacted with alkyl isocyanides to afford nitrile compounds in moderate to good yields. This protocol features broad functional group tolerance, simple reaction conditions, and gram-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Polyssena Renzi, Emanuele Azzi, Enrico Bessone, Giovanni Ghigo, Stefano Parisotto, Francesco Pellegrino, Annamaria Deagostino
Summary: An unprecedented visible light enhanced Heck reaction between aryl halides and allenyl tosyl amines has been reported in this study, using a simple catalytic system to produce arylated vinyl pyrrolidines and piperidines with high tolerance towards functional groups. The efficiency of this process is significantly influenced by electronic effects. Both experimental and computational mechanistic studies suggest a pivotal role of light in promoting the carbo-palladation step without evidence for a radical mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Multidisciplinary
Claire A. Herbert, Elizabeth R. Jarvo
Summary: This article describes the development of nickel-catalyzed reactions of alkyl alcohol derivatives to access C-(sp(3))-rich frameworks. Part I focuses on cross-coupling reactions, while Part II discusses stereoconvergent reactions. Part III explores the role of ligand identity in catalyst selectivity.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Medicinal
Irini Abdiaj, Santiago Canellas, Alejandro Dieguez, Maria Lourdes Linares, Brenda Pijper, Alberto Fontana, Raquel Rodriguez, Andres Trabanco, Eduardo Palao, Jesus Alcazar
Summary: In this study, an end-to-end process for increasing Fsp3 in bioactive molecules was reported, involving synthesis, work-up, purification, and post-purification with minimal human intervention using Negishi coupling. The protocol offers advantages such as automated sequential generation of organozinc reagents from alkyl halides, allowing a diverse range of alkyl groups to be functionalized via Pd-catalyzed Negishi coupling in continuous flow. Additionally, a fully automated liquid-liquid extraction was developed for unattended operations, and mass-triggered preparative HPLC facilitated efficient production of compounds with enriched sp3 character and better drug-like properties.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yu-jia Du, Xia-xin Sheng, Jun-hua Li, Jia-ming Chen, Sen Yang, Ming Chen
Summary: This article describes a palladium-catalyzed aryl-to-alkyl radical relay Heck reaction of amides at alpha-C(sp(3))-H sites with vinyl arenes. The reaction has a broad substrate scope and provides access to complex molecules. It is proposed that the reaction proceeds via a hybrid palladium-radical mechanism. The approach is expected to inspire the discovery of new palladium-catalyzed alkyl-Heck methods.
Article
Multidisciplinary Sciences
Pengfei Li, Chengcheng Guo, Siyi Wang, Dengke Ma, Tian Feng, Yanwei Wang, Youai Qiu
Summary: We reported a facile and general method for electroreductive deuteration of unactivated alkyl halides or pseudo-halides using D2O as the deuterium source. This method works well for various alkyl halides, including sterically hindered tertiary chlorides, and achieves high deuterium incorporation in organic synthesis.
NATURE COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Yulin Zhang, Yoshiaki Tanabe, Shogo Kuriyama, Ken Sakata, Yoshiaki Nishibayashi
Summary: Recently, transition metal-catalyzed enantioselective free radical substitution reactions have been recognized as convenient and important tools in synthetic chemistry. In this paper, we present a strategy to control enantioselective propargylic substitution reactions with alkyl radicals under photoredox conditions using a dual photoredox and diruthenium catalytic system. The successful example of transition metal-catalyzed enantioselective propargylic substitution reactions with free alkyl radicals is described.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Bartosz Gorski, Anne-Laure Barthelemy, James J. Douglas, Fabio Julia, Daniele Leonori
Summary: The study demonstrates an alternative amination strategy using alkyl iodides as radical precursors and copper catalysis to assemble sp3 C-N bonds at room temperature. This method provides S(N)2-like programmability and has been shown to be useful in the late-stage functionalization of pharmaceuticals for the preparation of valuable N-alkylated drug analogues.
Article
Infectious Diseases
Louis-Jerome Leba, Lise Musset, Stephane Pelleau, Yannick Estevez, Caroline Birer, Sebastien Briolant, Benoit Witkowski, Didier Menard, Michael J. Delves, Eric Legrand, Christophe Duplais, Jean Popovici
Article
Plant Sciences
Kevin Cottet, Yann Fromentin, Marina Kritsanida, Raphael Grougnet, Guillaume Odonne, Christophe Duplais, Sylvie Michel, Marie-Christine Lallemand
Article
Plant Sciences
Alexander E. Fox Ramos, Charlotte Alcover, Laurent Evanno, Alexandre Maciuk, Marc Litaudon, Christophe Duplais, Guillaume Bernadat, Jean-Francois Gallard, Jean-Christophe Jullian, Elisabeth Mouray, Philippe Grellier, Philippe M. Loiseau, Sebastien Pomel, Erwan Poupon, Pierre Champy, Mehdi A. Beniddir
JOURNAL OF NATURAL PRODUCTS
(2017)
Article
Biochemistry & Molecular Biology
Caroline Birer, Niklas Tysklind, Lucie Zinger, Christophe Duplais
MOLECULAR ECOLOGY RESOURCES
(2017)
Review
Biochemistry & Molecular Biology
Romain Duval, Christophe Duplais
NATURAL PRODUCT REPORTS
(2017)
Article
Parasitology
Louis-Jerome Leba, Jean Popovici, Yannick Estevez, Stephane Pelleau, Eric Legrand, Lise Musset, Christophe Duplais
INTERNATIONAL JOURNAL FOR PARASITOLOGY-DRUGS AND DRUG RESISTANCE
(2017)
Article
Chemistry, Analytical
Tingting Fu, David Touboul, Serge Della-Negra, Emeline Houel, Nadine Amusant, Christophe Duplais, Gregory L. Fisher, Alain Brunelle
ANALYTICAL CHEMISTRY
(2018)
Article
Multidisciplinary Sciences
Julie Bossu, Jacques Beauchene, Yannick Estevez, Christophe Duplais, Bruno Clair
Article
Multidisciplinary Sciences
Tingting Fu, Emeline Houel, Nadine Amusant, David Touboul, Gregory Genta-Jouve, Serge Della-Negra, Gregory L. Fisher, Alain Brunelle, Christophe Duplais
SCIENTIFIC REPORTS
(2019)
Article
Biochemistry & Molecular Biology
Caroline Birer, Corrie S. Moreau, Niklas Tysklind, Lucie Zinger, Christophe Duplais
Article
Multidisciplinary Sciences
Manuela O. Ramalho, Christophe Duplais, Jerome Orivel, Alain Dejean, Joshua C. Gibson, Andrew Suarez, Corrie S. Moreau
SCIENTIFIC REPORTS
(2020)
Editorial Material
Plant Sciences
Christophe Duplais, Nicolas Papon, Vincent Courdavault
TRENDS IN PLANT SCIENCE
(2020)
Article
Multidisciplinary Sciences
Christophe Duplais, Vincent Sarou-Kanian, Dominique Massiot, Alia Hassan, Barbara Perrone, Yannick Estevez, John T. Wertz, Estelle Martineau, Jonathan Farjon, Patrick Giraudeau, Corrie S. Moreau
Summary: The study on herbivorous turtle ants identifies the cuticular components that are nitrogen-enriched by gut bacteria, highlighting the important role of symbionts in insect evolution.
NATURE COMMUNICATIONS
(2021)
Article
Microbiology
Anais Chanson, Corrie S. Moreau, Christophe Duplais
Summary: This study reveals the high diversity of biosynthetic gene clusters (BGCs) producing specialized metabolites in the gut symbionts of Cephalotes ants, with different distribution patterns. Some symbionts may maintain a close spatial proximity in the gut and possess BGCs, while others may exist alone and lack BGCs.
FRONTIERS IN MICROBIOLOGY
(2021)
Article
Chemistry, Medicinal
Axel Touchard, Helen C. Mendel, Isabelle Boulogne, Volker Herzig, Nayara Braga Emidio, Glenn F. King, Mathilde Triquigneaux, Lucie Jaquillard, Remy Beroud, Michel De Waard, Olivier Delalande, Alain Dejean, Markus Muttenthaler, Christophe Duplais
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2020)
