Article
Multidisciplinary Sciences
Xianqing Wu, Chenglong Wang, Ning Liu, Jingping Qu, Yifeng Chen
Summary: Carbonylative reactions with CO gas are crucial in organic synthesis. In this study, the authors demonstrate a three-component tandem acylzincation/cyclization reaction using an earth-abundant nickel catalyst and 1 atm of CO gas under mild conditions.
NATURE COMMUNICATIONS
(2023)
Review
Chemistry, Multidisciplinary
Yair Cohen, Ilan Marek
Summary: The chemistry of cyclo-propane derivatives offers diverse challenges and interests researchers in theoretical, synthetic, and structural chemistry. Understanding the unique properties and novel synthesis methods of these small rings is crucial for the field, with a focus on the stereoselective synthesis of polysubstituted cyclopropanes.
ACCOUNTS OF CHEMICAL RESEARCH
(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, Organic
Li-Chen Xu, Xiao-Di Ma, Kun-Ming Liu, Xin-Fang Duan
Summary: In this study, a new method is proposed to achieve regioselective alkylation of pyridines at the C2 position, providing an important synthetic tool for late-stage diversification of drugs.
Article
Chemistry, Multidisciplinary
Rin Seki, Naofumi Hara, Teruhiko Saito, Yoshiaki Nakao
Summary: In this study, we reported a novel rhodium catalyst with X-type PAlP pincer ligand for catalytic reduction of a C-O bond and borylation. The reaction mechanism was revealed through characterization of reaction intermediate and deuterium-labeling experiments. This catalytic system demonstrated steric-hindrance-dependent chemoselectivity, providing a new strategy for selective C-O bond activation through heterobimetallic catalysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
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
Chongyang Wu, Tao Ying, Hangqian Fan, Chenhui Hu, Weike Su, Jingbo Yu
Summary: A mechanochmically activated magnesium(0) metal has been developed as a highly active mediator for direct C-4-H alkylation of pyridines with alkyl halides. The method demonstrates excellent regioselectivity and substrate scope, including those containing reducible functionalities, free amines, alcohols, and biologically relevant molecules, leading to the formation of 4-alkylpyridine products. Preliminary mechanistic studies suggest a radical-radical coupling pathway.
Article
Chemistry, Organic
Chongyang Wu, Tao Ying, Hangqian Fan, Chenhui Hu, Weike Su, Jingbo Yu
Summary: A method for direct C-4-H alkylation of pyridines with alkyl halides using mechanochemically activated magnesium(0) metal as a highly active mediator has been developed. This method exhibits excellent regioselectivity and broad substrate scope, including reducible functionalities, free amines, alcohols, and biologically relevant molecules, enabling the synthesis of 4-alkylpyridine products. Preliminary mechanistic studies suggest a radical-radical coupling pathway.
Article
Chemistry, Multidisciplinary
A. Hess, H. C. Guelen, N. Alandini, A. Mourati, Y. C. Guersoy, P. Knochel
Summary: This study presents a novel method for the selective ortho, ortho'-functionalization of readily available aryl oxazolines using sBu(2)Mg in toluene followed by trapping reactions with electrophiles. The conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed for the reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
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, Multidisciplinary
Hyotaik Kang, Chao-Jun Li
Summary: This study presents the use of umpolung aldehydes as carbanion equivalents for highly regioselective 1,6-conjugate addition reactions to unsaturated ketones, with initial investigation into the enantioselective variant. It was found that the synergy of ruthenium(ii) catalyst and electron-rich, bidentate phosphine ligand is crucial for enhancing reactivity and selectivity under mild reaction conditions.
Article
Chemistry, Multidisciplinary
Yang Gao, Simin Yang, Minwei She, Jianhong Nie, Yanping Huo, Qian Chen, Xianwei Li, Xiao-Qiang Hu
Summary: We report a practical route for the synthesis of valuable 3-aryl anthranils from readily available anthranils and simple arenes using electrophilic aromatic substitution (EAS) strategy. The method shows good compatibility with a wide range of arenes and delivers various structurally diversified 3-aryl anthranils in good yields and high regioselectivity. The synthesized 3-aryl anthranils are proven to be a highly robust platform for accessing biologically active compounds, drug derivatives, and organic optoelectronic materials.
Article
Chemistry, Inorganic & Nuclear
Fei Fan, Lixing Zhao, Meiming Luo, Xiaoming Zeng
Summary: Chemically inert C(aryl)-F bonds have been successfully cleaved and coupled with unreactive C(aryl)-O bonds using chromium catalysis, enabling high selectivity and efficiency for cross-electrophile coupling.
Article
Chemistry, Organic
Miseon Lee, Dennis Sulwey, Madeline E. Rotella, Wan Shin Kim, Xuan Ju, Qi Jiang, Marisa C. Kozlowski, Jaehee Lee
Summary: This study reports the copper catalyzed selective and stereospecific opening of CF3-aziridines. The focus is on the synthesis of α-CF3-β-arylethylamines, which can serve as important intermediates for the synthesis of synthetic analogues and biologically active molecules. Density functional theory calculations provide insights into the active copper species and the role of LiClMgX (X = Cl or I) as a Lewis acid. Furthermore, the computed mechanism explains the high regioselectivity of this transformation.
Article
Chemistry, Multidisciplinary
Hao Liang, James P. Morken
Summary: Enantioenriched tertiary alkylboronic esters can be activated by in situ generated adamantyllithium, leading to stereoretentive boron-to-copper transmetalation. The resulting alkylcopper species can react with various electrophiles through cross-coupling reactions, providing synthetically useful compounds with quaternary stereocenters. DFT calculations of the transmetalation process offer insights into reactivity and selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
