Letter
Chemistry, Organic
Panchi Guo, Hao Jin, Jinhui Han, Liang Xu, Pengfei Li, Miao Zhan
Summary: This study demonstrates a nickel-catalyzed Negishi cross-coupling reaction for the synthesis of versatile organoboron products with high functional-group tolerance. The reaction allows for the coupling of unactivated tertiary alkyl electrophiles with boron-stabilized organozinc reagents. The importance of the Bpin group in accessing the quaternary carbon center is highlighted, and the practicality of the prepared quaternary organoboronates is showcased through their conversion to other useful compounds.
Article
Chemistry, Organic
Jiabao Wang, Yuxin Gong, Deli Sun, Hegui Gong
Summary: A Ni-catalyzed reductive cross-coupling reaction has been developed for the construction of benzylated all-carbon quaternary centers. The reaction yields moderate to excellent results with high functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Quentin D. Tercenio, Erik J. Alexanian
Summary: The nickel-catalyzed reductive coupling of allyl alcohols with chiral, nonracemic alkyl tosylates reported in this study delivers valuable allylation products with high levels of stereospecificity across a range of substrates. The catalytic system, consisting of a simple nickel salt and a commercially available reductant, represents a rare example of a cross-coupling involving the C-O bonds of two electrophiles.
Article
Chemistry, Organic
Kaluvu Balaraman, Christian Wolf
Summary: The Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been successfully achieved through mechanistically distinct Pd and Ni catalyzed pathways, demonstrating superiority over competing reactions in over 20 examples. The potential utility of this method is showcased in various compounds, including heterocyclic structures, 1,1-disubstituted and trans-1,2-disubstituted alkenes.
Article
Chemistry, Organic
Ikuya Fujii, Kazuhiko Semba, Yoshiaki Nakao
Summary: Rhodium-aluminum bimetallic complexes catalyze the Kumada-Tamao-Corriu (KTC) cross-coupling reaction using arylmagnesium compounds generated from corresponding aryl fluorides or chlorides. This method allows the challenging KTC coupling reaction to be carried out using aryl fluorides as nucleophiles, resulting in various biaryls.
Article
Chemistry, Multidisciplinary
Ruofei Cheng, Graham de Ruiter, Chao-Jun Li
Summary: Cobalt-based catalysts have shown unique advantages in cross-coupling reactions, with higher catalytic activity and lower toxicity compared to palladium and nickel catalysts. A novel cobalt-catalyzed alkyl-alkyl cross-coupling reaction of hydrazone with alkyl halides has been developed under mild reaction conditions, using a PNP-type pincer ligand as an essential catalyst. Both aldehyde and ketone hydrazones are compatible with this reaction, producing a series of C(sp(3))-C(sp(3)) coupling products in moderate to good yields.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Giuseppe Dilauro, Francesco Messa, Fabio Bona, Serena Perrone, Antonio Salomone
Summary: A simple cobalt complex, Co(phen)Cl₂, has been found to be a highly efficient and cost-effective precatalyst for various cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl, and alkyl bromides. New C(sp²)-C(sp²) and C(sp²)-C(sp³) bonds can be formed in good to excellent yields and high chemoselectivity under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yu-Feng Zhang, Xiao-Yang Dong, Jiang-Tao Cheng, Ning-Yuan Yang, Li-Lei Wang, Fu-Li Wang, Cheng Luan, Juan Liu, Zhong-Liang Li, Qiang-Shuai Gu, Xin-Yuan Liu
Summary: This study demonstrates the successful use of sulfoximines as ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides, achieving high yields and enantioselectivity. The obtained alpha-chiral primary amines can be converted to various synthetic building blocks, ligands, and drugs, highlighting the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Inorganic & Nuclear
Aiping Fu, Lixing Zhao, Chao Li, Meiming Luo, Xiaoming Zeng
Summary: The chromium-catalyzed borylative coupling between aliphatic bromides and HBpin has been successfully achieved with the use of CrCl3, 4,4'-di-tert-butyl-2,2'-dipyridyl, and aluminum. Mechanistic studies reveal the crucial role of aluminum in generating reactive Cr species and aliphatic radicals, which leads to the formation of borylated alkanes.
Article
Chemistry, Organic
Bryan C. Figula, D. Lucas Kane, Kaluvu Balaraman, Christian Wolf
Summary: Cross-coupling of alkyl fluorides and organocuprates is achieved via aluminum halide mediated C-F bond activation, leading to the formation of Csp2-Csp3 and Csp3-Csp3 bonds. The reaction exhibits mild conditions and effectively controls competing side reactions, resulting in high yields and good functional group tolerance.
Article
Chemistry, Organic
Xuan-Di Song, Meng-Meng Guo, Shuang Xu, Chuanji Shen, Xiaocong Zhou, Xue-Qiang Chu, Mengtao Ma, Zhi-Liang Shen
Summary: A nickel-catalyzed direct reductive cross-coupling of disubstituted cycloalkyl iodides with aryl iodides was developed, allowing for efficient stereocontrolled synthesis of a variety of cross-coupled products with high diastereoselectivity and wide functional group tolerance. The one-pot reaction is simple to operate, providing a convenient method for the synthesis of complex molecules.
Article
Chemistry, Organic
Peter G. N. Neate, Bufan Zhang, Jessica Conforti, William W. Brennessel, Michael L. Neidig
Summary: Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, allowing for diverse coupling reactions without significant modification of the catalytic protocol. This represents a rare example of a single iron-catalyzed system effective across various coupling reactions while remaining operationally simple.
Article
Chemistry, Multidisciplinary
Pan Pan, Shihan Liu, Yu Lan, Huiying Zeng, Chao-Jun Li
Summary: A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. Hydrazones were used as alternatives to organometallic reagents, making this cross-coupling mild and green. Mechanistic investigations revealed the formation of an electron donor-acceptor complex, generating an aryl radical via single-electron transfer.
Article
Chemistry, Organic
Hao Xu, Cai-Yu He, Bo-Jie Huo, Jia-Wen Jing, Chengping Miao, Weidong Rao, Xue-Qiang Chu, Xiaocong Zhou, Zhi-Liang Shen
Summary: In this study, a cross-electrophile coupling of aryl thiols with aryl bromides was reported, where C-S bond activation occurred instead of S-H bond cleavage, leading to the formation of thioethers as the major products. The reaction proceeded effectively with a nickel catalyst, magnesium turnings, and lithium chloride in THF at room temperature, and a variety of structurally diverse biaryls were obtained in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Cole L. Cruz, John Montgomery
Summary: A mild and convenient coupling reaction between aliphatic aldehydes and unactivated alkyl bromides has been developed using a common Ni(II) precatalyst and a readily available bioxazoline ligand, affording silyl-protected secondary alcohols. The reaction is operationally simple, utilizes Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. The presence of 1,5-hexadiene as an additive plays a crucial role in optimizing yields.
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)