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, Physical
Sanita B. Tailor, Mattia Manzotti, Gavin J. Smith, Sean A. Davis, Robin B. Bedford
Summary: The cobalt-catalyzed Suzuki biaryl cross-coupling reaction using alkoxide bases, with strict stoichiometric control and selection of the right boron ester, is shown to be achievable. Excessive alkoxide bases or lithium additives can inhibit or poison the catalyst, while a neopentane diol-based boron ester is crucial for optimal performance.Mechanistic and computational studies have been carried out to investigate the reaction mechanism and explain unexpected observations.
Article
Chemistry, Multidisciplinary
Xiaomin Shu, De Zhong, Yanmei Lin, Xiao Qin, Haohua Huo
Summary: We report a general and modular approach for the direct enantioselective alpha-arylation of saturated azacycles and acyclic N-alkyl benzamides via nickel/photoredox dual catalysis. This method requires no oxidants or organometallic reagents, features broad substrate scope and high enantioselectivities, and is applicable to late-stage diversification of medicinally relevant complex molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Bijan Mirabi, Austin D. Marchese, Mark Lautens
Summary: In this study, a nickel-catalyzed cross-electrophile coupling reaction of aryl chlorides and heteroaryl chlorides was reported, enabled by a synergistic combination of halide effects and the addition of a magnesium salt. Electronic-deficient aryl chlorides were found to perform the best in the reaction, and preliminary mechanistic evidence showed that MgCl2 is crucial for accelerating the reduction of Ni(II) while small quantities of iodide lead to improved yields.
Article
Chemistry, Multidisciplinary
Yu Chen, Xiao Zhang, Fang Liu, Gucheng He, Ju Zhang, K. N. Houk, Amos B. Smith, Yong Liang
Summary: CuI plays a crucial role in siloxane-mediated Pd-catalyzed cross-coupling reactions by accelerating the transmetalation process of the organosilicon intermediate. CuI2 acts as a shuttle between the Si-Cu(I) and Cu(I)-Pd(II) transmetalation processes.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Yu-Zhong Yang, Yang Li, Gui-Fen Lv, De-Liang He, Jin-Heng Li
Summary: A nickel-catalyzed C-S reductive cross-coupling reaction has been developed for the synthesis of alkyl aryl thioethers from alkyl halides and arylthiosilanes. This reaction involves umpolung transformations of arylthiosilanes followed by C-S reductive cross-coupling with alkyl halides to form C(sp(3))-S bond. It exhibits exquisite chemoselectivity, excellent tolerance of diverse functional groups, and wide applications for the late-stage modification of biologically relevant molecules.
Article
Chemistry, Multidisciplinary
Linlin Ding, Yue Zhao, Hongjian Lu, Zhuangzhi Shi, Minyan Wang
Summary: For the first time, a catalytic enantioselective propargyl-aryl cross-coupling between two electrophiles was achieved in a stereoconvergent manner. The potential utility of this conversion is demonstrated in the facile construction of stereoenriched bioactive molecule derivatives and medicinal compounds based on the diversity of acetylenic chemistry. Detailed experimental studies have revealed the key mechanistic features of this transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Tamae Seo, Koji Kubota, Hajime Ito
Summary: Mechanochemical synthesis using transition-metal catalysts has advantages such as low solvent waste and short reaction times. However, the direct use of transition-metal catalysts in mechanochemical reactions without modifications limits the development of efficient cross-coupling processes. This study presents a new approach, using mechanochemistry-directed design to develop ligands for Suzuki-Miyaura cross-coupling reactions. The embedding of the ligand into a poly(ethylene glycol) polymer prevents catalyst deactivation and shows high catalytic activity at room temperature.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Fusheng Bie, Xuejing Liu, Han Cao, Yijun Shi, Tongliang Zhou, Michal Szostak, Chengwei Liu
Summary: The Pd-catalyzed double-decarbonylative synthesis of aryl thioethers involves an aryl exchange reaction between amides and thioesters, with amides serving as aryl donors and thioesters as sulfide donors. The use of Pd/Xantphos without any additives promotes aryl exchange by C(O)-N/C(O)-S cleavages, allowing for a wide variety of amides and sulfides to be used in the reaction.
Article
Chemistry, Organic
Yi-Bing Yin, Xiao-Shui Peng, Henry N. C. Wong
Summary: A one-pot iron-catalyzed cross-coupling protocol was developed for the synthesis of unsymmetrical biaryls using aryl chlorides, aryl bromides, and magnesium metal. The key step in this reaction is the in situ generation of Grignard reagents.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Aleksandra Blocka, Jakub Ostapko, Wojciech Chaladaj
Summary: For the first time, a cascade reaction involving a 5-exo-dig intramolecular nucleophilic addition of an enamine to a terminal alkyne followed by cross coupling has been demonstrated. This reaction allows for the stereoselective formation of two new C-C bonds using a single Pd-complex capable of catalyzing two mechanistically diverse transformations. Mechanistic investigations revealed that cyclization, relying on the facile displacement of OTf weakly bound to the Pd-center by the alkyne, is the rate limiting step.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Lyudmila A. Grishchenko, Lidiya N. Parshina, Lyudmila I. Larina, Yana A. Kostyro, Boris A. Trofimov
Summary: New salicylate derivatives of arabinogalactan have been synthesized with high yield, showing high anti-coagulation activity. The reaction yield varies depending on the base used, and unexpected additional reactions were observed in the presence of piperidine.
CARBOHYDRATE POLYMERS
(2021)
Article
Chemistry, Organic
Dejiang Zhang, Zhi Xu, Ting Tang, Liyuan Le, Cairong Wang, Nobuaki Kambe, Renhua Qiu
Summary: In this study, a general method for the synthesis of unsymmetric diarylmethanes from (hetero)aryl methylhalides and Sb-aryl stibines is described. The protocol has a broad substrate scope and good functional group tolerance. Gram-scale synthesis of drug molecules and their derivatives was efficiently achieved using this method.
Article
Chemistry, Organic
Maddali L. N. Rao, Sachchida Nand
Summary: The threefold cross-coupling of triarylbismuth reagents with 4-chloro-3-formylcoumarins using Pd-catalyzed conditions successfully provided the corresponding 4-aryl-3-formylcoumarins in a chemoselective manner with high yields. This method was applicable to electronically different triarylbismuth reagents and 4-chloro-3-formylcoumarins while preserving the 3-formyl group in the coumarin scaffold.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Meng-Yu Xu, Bin Xiao
Summary: Palladium-catalyzed cross-coupling reactions play a crucial role in the complex synthetic field. Our research group focuses on developing new germanium-based reagents and catalytic processes. Over the past three years, we have established new methods for the synthesis of novel compounds, with particular emphasis on the unique properties of alkyl carbagermatranes.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
