Article
Chemistry, Organic
Ranran Cui, Yinqi Wang, Liyan Yuwen, Li Gao, Zhuo Huang, Wei-Han Wang, Qing-Wei Zhang
Summary: In this study, a novel Ni(II)-catalyzed asymmetric C-P cross-coupling reaction is developed for the synthesis of valuable chiral heterocyclic tertiary phosphine oxides. The method is mild, efficient, and does not require an external reductant, light irradiation, or electricity.
Article
Biochemistry & Molecular Biology
Dezhi Lin, Yunfang Liu, Hongyu Yang, Xiao Zhang, Huaming Sun, Yajun Jian, Weiqiang Zhang, Jianming Yang, Ziwei Gao
Summary: This research presents a highly selective C-O activation approach for the synthesis of cross-conjugated enynones using alpha, beta-unsaturated triazine esters as acyl electrophiles. Under base and phosphine ligand-free conditions, NHC-Pd(II)-Allyl precatalyst alone efficiently catalyzed the cross-coupling reaction of alpha, beta-unsaturated triazine esters with terminal alkynes, yielding 31 cross-conjugated enynones with diverse functional groups. This method showcases the potential of triazine-mediated C-O activation for the preparation of highly functionalized ketones.
Article
Nanoscience & Nanotechnology
Chidharth Krishnaraj, Himanshu Sekhar Jena, Kuber Singh Rawat, Johannes Schmidt, Karen Leus, Veronique Van Speybroeck, Pascal Van Der Voort
Summary: This study synthesized and compared the performance of 2D imine COFs as catalysts, finding that Pd@TTA-DFB COF exhibited fast reactivity but low stability, Pd@TTA-DFP COF had the highest stability but slowest reactivity, and Pd@TTA-TBD COF showed the best overall performance. Experimental and computational results indicated that the reduction from Pd(II) to Pd(0) is a key step in determining the catalytic activity of COFs.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Organic
Benedikt Kolb, Daniela Silva dos Santos, Sanja Krause, Anna Zens, Sabine Laschat
Summary: In this article, a new stereospecific sequential hydrozirconation/Pd-catalyzed acylation reaction was reported for the synthesis of conjugated (2E,4E)-dienones. Regardless of the substitution pattern, the reaction could selectively form the corresponding dienones under mild conditions. Furthermore, this method was successfully applied to the synthesis of non-natural and natural dienone-containing terpenes.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Yong Wang, Wenmin Pang, Shaojie Zhang, Chen Tan
Summary: A series of N-containing phosphine-sulfonate palladium complexes were synthesized and used as stimuli-responsive catalysts in ethylene polymerization, demonstrating improved catalytic performances and high-molecular-weight polyethylene products. Metal Lewis acids were found to interact with the N-containing moieties on the catalysts, providing a simple and versatile strategy for tuning the properties of olefin polymerization catalysts.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Minghui Zhu, Qinglong Zhang, Weiwei Zi
Summary: The study presents a dual-metal catalyzed diastereodivergent coupling method for the synthesis of beta-amino alcohols with multiple stereoisomers, enabling the concise preparation of natural products such as mycestericins F and G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Logan E. Vine, Ryan D. Reeves, Eleanor M. Landwehr, Israel Fernandez, Jennifer M. Schomaker
Summary: This study demonstrates predictable control over the mechanism of Pd-catalyzed allene cross-coupling/cyclization and cycloisomerization by targeted changes to the reaction conditions, resulting in the successful access to enantioenriched cyclopropanes and cyclopentenes. Furthermore, it shows a simple switch of the ligand on Pd can divert the reactivity of allenyl malonate from cross-coupling/cyclization to cycloisomerization.
Article
Chemistry, Multidisciplinary
Sheng Zhang, Junchao Yin, Ziyang Wang, Yang Li, Yukang Fu, Ji Ma, Zhilong Xie, Ming Bao
Summary: A palladium-catalysed aromative benzylic allylation and allenylation of benzyl chlorides with allyl and allenyl pinacolborates is reported for the first time. The reactions are conducted smoothly in the presence of a bidentate phosphine ligand, yielding good cross-coupling products. This new synthetic method exhibits excellent tolerance for various functional groups and is compatible with sensitive groups such as NO2, CF3, CN, and COOMe. The utilization of a bidentate ligand and heating is crucial for the transformation. DFT calculation results reveal the importance of wide-bite-angle bidentate ligands for the formation of an eta(1)-benzyl-eta(1)-allylpalladium intermediate and the thermodynamic favorability of the normal coupling reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Felipe Verdugo, Ricardo Rodino, Martin Calvelo, Jose Luis Mascarenas, Fernando Lopez
Summary: The reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) can be directed towards tandem cycloisomerization/cross-coupling processes by using Pd-0 catalysts with phosphorus-based monodentate ligands. This allows for the synthesis of a wide variety of highly functionalized cyclic alcohols and amines through the formation of key pi-allyl oxapalladacyclic intermediates which are trapped with external nucleophilic partners.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Daniel Sowa Prendes, Florian Papp, Nagesh Sankaran, Nardana Sivendran, Frederike Beyer, Christian Merten, Lukas J. Goossen
Summary: Arylglycines, which are important pharmacophores in several top-selling drugs, can now be synthesized from abundant aryl chlorides using a Pd-catalyzed Schollkopf-type amino acid synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Dejiang Zhang, Liyuan Le, Renhua Qiu, Wai-Yeung Wong, Nobuaki Kambe
Summary: A strategy for the formation of antimony-carbon bond via nickel-catalyzed cross-coupling of halostibines was developed. This method has a wide substrate scope and is compatible with various functional groups. The successful synthesis of arylated stibine demonstrated the high synthetic potential of this transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Chuanyong Wang, Xiaobo Hu, Cheng Xu, Qiangqiang Ge, Qingliang Yang, Jianqi Xiong, Wei-Liang Duan
Summary: A novel nickel-catalyzed enantioselective C(sp(2))-P cross-coupling has been developed for the synthesis of P-stereogenic phosphine oxides. The reaction of racemic secondary phosphine oxides with alkenyl/aryl bromides produces P-stereogenic phosphine oxides with high yields and enantioselectivities. The method shows excellent tolerance towards various functional groups and has been applied for late-stage functionalization and product transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Sheng-Qi Qiu, Yu Chen, Xiang-Jun Peng, Shi-Jiang He, Jun Kee Cheng, Yong-Bin Wang, Shao-Hua Xiang, Jun Song, Peiyuan Yu, Junmin Zhang, Bin Tan
Summary: In this study, we achieved the arene-alkene Suzuki-Miyaura coupling reaction between hindered aryl halides and vinyl boronates by designing appropriate ligands and reaction parameters. The axially chiral acyclic aryl-alkenes obtained exhibited remarkable efficiency, enantioselectivity, and E/Z selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Xiaoyan Wu, Junjie Fan, Xin Huang, Shengming Ma
Summary: An unexpected rhodium-catalyzed reaction has been reported for the synthesis of specific compounds with high efficiency, showing great potential for further research and applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Biochemistry & Molecular Biology
Lucia Veltri, Roberta Amuso, Raffaella Mancuso, Bartolo Gabriele
Summary: This short review highlights the progress in utilizing palladium-catalyzed carbon dioxide for synthesizing valuable organic molecules. The review is organized based on the type of substrate used in the Pd-catalyzed carboxylation process, including olefinic substrates, acetylenic substrates, and other substrates such as aryl halides and triflates.