Article
Chemistry, Organic
Qian Ye, Wencheng Huang, Li Wei, Mingzhong Cai
Summary: A highly efficient heterogeneous copper(I)-catalyzed cross-coupling of trialkylsilylethynes with N-tosylhydrazones has been achieved using SBA-15-immobilized L-proline-Cu(I) complex as the catalyst and (LiOBu)-Bu-t as the base. The reaction occurs in dioxane at 90-110 degrees C and leads to the formation of C(sp)-C(sp(3)) bonds with moderate to high yields. The recyclable nature of the immobilized copper(I) complex allows for up to 12 repeated uses without significant loss of activity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kun Wu, Chuan Wu, Xiao-Ying Jia, Lin Zhou, Qing-Han Li
Summary: This study successfully developed a highly efficient method for the synthesis of aryl substituted conjugated enediynes and unsymmetrical 1,3-diynes through selective cross-coupling reactions. The research found that although alkyl substituted products were not obtained, the same starting materials could selectively produce the desired products in different catalytic systems.
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, 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, 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
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, Multidisciplinary
Daniels Posevins, Aitor Bermejo-Lopez, Jan-E. Backvall
Summary: An iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents was disclosed, allowing for efficient chirality transfer and preparation of various fluoroalkyl allenes. Additionally, an iron-catalyzed cross-coupling of Grignard reagents with alpha-alkynyl oxetanes and tetrahydrofurans was demonstrated as a straightforward approach towards fully substituted beta- or gamma-allenols.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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
Peng Chen, Zhi-Yong Wang, Xiao-Shui Peng, Henry N. C. Wong
Summary: An efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners is presented. Over 30 examples were obtained with moderate to good yields and high stereo-selectivities. The practicality of this method is evidenced by a gramscale synthesis, and a preliminary mechanistic investigation was also performed.
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, Organic
Yihang Li, Jia Sheng Ng, Bin Wang, Shunsuke Chiba
Summary: A protocol for synthesizing alpha-alkynylnitrones from 1,3-enynes has been developed using MgH2 triggered hydromagnesiation. The resulting alpha-alkynylnitrones can serve as versatile precursors for constructing various nitrogen-containing compounds.
Article
Chemistry, Multidisciplinary
Nikki J. Bakas, Pablo Chourreu, Eric Gayon, Guillaume Lefevre, Michael L. Neidig
Summary: The molecular-level role of alkoxide salts as alternative additives in iron-catalyzed cross-coupling reactions is investigated. Spectroscopic studies reveal that alkoxides promote the formation of homoleptic organoferrates, providing a non-toxic alternative to N-methylpyrrolidone for accessing reactive intermediates.
CHEMICAL COMMUNICATIONS
(2023)
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)
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
Multidisciplinary Sciences
Eiji Shirakawa, Yuki Ota, Kyohei Yonekura, Keisho Okura, Sahiro Mizusawa, Sujan Kumar Sarkar, Manabu Abe
Summary: An electron has been found to catalyze the cross-coupling reaction of organometallic compounds with aryl halides, which is more desirable for green and sustainable chemistry compared to transition metal catalysis. However, high temperature is required for this electron catalysis. We discovered that visible light photoirradiation can accelerate the electron-catalyzed reaction by using photoredox catalysis, enabling the reaction to proceed at room temperature. The supply of the electron catalyst through photoredox catalysis also expands the scope of aryl halides.
Article
Chemistry, Multidisciplinary
Julien Buendia, Benjamin Darses, Philippe Dauban
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Julien Buendia, Gwendal Grelier, Benjamin Darses, Amanda G. Jarvis, Frederic Taran, Philippe Dauban
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Julien Buendia, Zong Chang, Hendrik Eijsberg, Regis Guillot, Angelo Frongia, Francesco Secci, Juan Xie, Sylvie Robin, Thomas Boddaert, David J. Aitken
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Gerard Cahiez, Christophe Duplais, Julien Buendia
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2009)
Review
Chemistry, Multidisciplinary
Gerard Cahiez, Christophe Duplais, Julien Buendia
Article
Chemistry, Multidisciplinary
Julien Buendia, Jakob Mottweiler, Carsten Bolm
CHEMISTRY-A EUROPEAN JOURNAL
(2011)
Article
Chemistry, Multidisciplinary
Gerard Cahiez, Olivier Gager, Julien Buendia, Cindy Patinote
CHEMISTRY-A EUROPEAN JOURNAL
(2012)
Article
Chemistry, Multidisciplinary
Tillmann Kleine, Julien Buendia, Carsten Bolm
Article
Chemistry, Organic
Gerard Cahiez, Olivier Gager, Julien Buendia
Article
Chemistry, Physical
Sandra Abi Fayssal, Timothee Naret, Vincent Huc, Julien Buendia, Cyril Martini, Emmanuelle Schulz
Summary: The scalable synthesis of Pd-NHC cinnamyl complexes supported on benzyloxycalix[8]arene is reported. These catalysts are highly active for Buchwald-Hartwig cross-coupling reactions, enabling the coupling of aryl chlorides and bromides with alkyl and aryl amines at low catalytic loadings. The supported complexes also produce attractive unsymmetrical triarylamines and can even facilitate the synthesis of unprecedented Pd-catalyzed C-H activation products. Through an easy to implement procedure, these characterized catalysts combine the best features of homogeneous and heterogeneous catalysis, achieving high efficiency and low Pd leaching levels.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Axel Labattut, Sandra Abi Fayssal, Julien Buendia, Ibrahim Abdellah, Vincent Huc, Cyril Martini, Emmanuelle Schulz
REACTION CHEMISTRY & ENGINEERING
(2020)
Article
Chemistry, Multidisciplinary
Gerard Cahiez, Alban Moyeux, Julien Buendia, Christophe Duplais
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2007)
