Article
Chemistry, Organic
Qingkun Wu, Jingxuan Hou, Qingshan Gu, Hui Gao, Meiqi Shi, Lu Zheng
Summary: A PhI(OAc)(2)/Pd(OAc)(2) system has been developed that synergistically promotes the formation of 8-hydroxyquinoline derivatives from benzoxazoles and alcohols. The reaction proceeds smoothly with a variety of benzoxazoles and alcohols, giving moderate yields of the corresponding 8-hydroxyquinoline derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jian Wang, Changqing Tu, Mei-Lin Feng, Nan Li
Summary: A metal-free reaction system utilizing TEMPO and PhI(OAc)(2) has been developed for the oxidative C-N coupling of benzoxazoles with NH-sulfoximines, resulting in moderate to high yields of corresponding 2-iminoazoles under ambient atmosphere without any metal catalyst at room temperature.
Article
Chemistry, Multidisciplinary
Dongchao Zhang, Dali Yang, Shengchun Wang, Li Zeng, Jie Xin, Heng Zhang, Aiwen Lei
Summary: This study investigated the structure of palladium acetate in solution using X-ray absorption fine structure (XAFS) spectroscopy, revealing that monomer is the main form for Pd(OAc)(2) in various solvents. Additionally, Pd(II) can be reduced to Pd(0) in ethanol solution. The structural information obtained will help in understanding the mechanism of Pd(OAc)(2) involved organic reactions.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Alexios G. Stamoulis, Peng Geng, Michael A. Schmidt, Martin D. Eastgate, Alina Borovika, Kenneth J. Fraunhoffer, Shannon S. Stahl
Summary: The study developed a method for the diacyloxylation of cyclohexadiene by pairing catalytic BQ with tert-butyl hydroperoxide and catalytic quantities of bromide, enabling a switch in selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Caitlin Kozack, Stephen J. Tereniak, Jonathan N. Jaworski, Bao Li, David L. Bruns, Spring M. M. Knapp, Clark R. Landis, Shannon S. Stahl
Summary: This study focuses on the impact of benzoquinone on the catalytic activity in palladium(II)-catalyzed allylic acetoxylation. The results indicate that benzoquinone enhances the performance of the catalyst, showing a synergistic effect with Co(salophen) in improving reaction performance. The mechanistic studies suggest that both benzoquinone and oxygen play significant roles in oxidizing Pd(0) to Pd(II), leading to better reaction outcomes.
Article
Chemistry, Multidisciplinary
Liwei Wang, Dali Yang, Hesham Alhumade, Hong Yi, Xiaotian Qi, Aiwen Lei
Summary: This study investigated the real structures of Pd catalyst in solution with various inorganic halogen additives using XAFS spectroscopy and cyclic voltammetry. The results showed that the inorganic halide additives played a crucial role in Pd catalysis.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Yongliang Tu, Duo Zhang, Peng Shi, Chenyang Wang, Ding Ma, Carsten Bolm
Summary: Visible light-induced C-C bond cleavage of ketones allows for N-acylation of sulfoximines without the need for a (photo)catalyst, at ambient temperature in air. The method has a broad substrate scope for both ketones and sulfoximines, with NBS essential for converting NH-sulfoximines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Farshad Shiri, Alireza Ariafard
Summary: 1,6-enynes can be cyclized to yield cyclopropyl ketones using PhI(OAc)(2) (PIDA) in the presence of Pd(OAc)(2) as a catalyst. However, when 1,6-enynes are substituted by a hydroxy group at the alpha-position, polycyclic oxa-heterocycles are formed instead. This study aims to investigate the mechanistic aspects of these transformations and reveals that the change in chemoselectivity is due to the electronic nature of the Pd catalyst changing from pi-philicity to oxophilicity during the catalytic cycle.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Hui-Ju Chen, Chien-Cheng Chiu, Tsui Wang, Dong-Sheng Lee, Ta-Jung Lu
Summary: The bis-NHC-Ag/Pd(OAc)(2) catalytic system is an intelligent catalyst that can efficiently reduce various functional groups to good to excellent yields, with high selectivity for different functional groups. In addition, the system can achieve stereoselective transformation of alkynes to alkenes in aqueous media, providing a simple operational protocol for reducing functional groups.
Article
Chemistry, Organic
Lin Huang, Li-Ping Chen, Yu Du, Mao-Ying Fang, Bi-Qin Wang, Chun Feng, Shi-Kai Xiang
Summary: The annulative pi-extension of o-iodobiphenyls with aliphatic anhydrides in the bay-region leads to efficient synthesis of phenanthrol derivatives. Control experiments suggest dibenzopalladacyclopentadienes as reaction intermediates.
Article
Chemistry, Physical
Kaveh Farshadfar, Samaneh K. Tizhoush, Alireza Ariafard
Summary: This study provides a detailed explanation for the observation that Bronsted acids can promote Pd-catalyzed functionalization of C-H bonds. Density functional theory calculations show that the presence of Bronsted acid reduces the energy barrier for C-H activation, leading to accelerated reactions.
Article
Biochemistry & Molecular Biology
Yuxuan Zhang, Zheng Wei, Evgeny V. Dikarev
Summary: The paper describes a heterobimetallic hexanuclear precursor designed to accommodate 5-coordinated sodium ions. The structure and composition of the complex have been confirmed using various techniques. Additionally, the compound can be used as a precursor for the synthesis of sodium-ion oxide cathode materials.
Article
Chemistry, Organic
Taiga Yurino, Sunaho Saito, Mizuki Ichihashi, Takeshi Ohkuma
Summary: A Pd(OAc)(2)/P(OPh)(3) combination catalyst was used for the Tsuji-Trost-type allylic amination under aerobic conditions, and it was found that the reaction proceeded efficiently only when allylic phosphates were employed as electrophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zenghui Sun, Xinhang Zhang, Jiayue Fu, Lianjie Zhang, Maosheng Cheng, Lu Yang, Yongxiang Liu
Summary: In this study, six 8-oxoprotoberberines were synthesized collectively in four steps with acceptable yields (14-19%), including 8-oxopalmatine, 8-oxopseudopalmatine, 8-oxoberberine, and 8-oxopseudoberberine. The synthetic route involved In-(OTf)(3)-catalyzed cyclization and Heck coupling. Additionally, the syntheses of natural products berberine, canadine, and iambertine were achieved via reductions of 8-oxoberberine, providing a concise approach to the synthesis of these alkaloids.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dong-Fang Jiang, Zhenjie Qi, Dengfeng Li, Si-Miaomiao Wen, Zhao Liu, Wen-Juan Hao, Bo Jiang
Summary: This study presents a metal-free protocol for the direct construction of C(sp(2))-N and C-O bonds via a PhI(OAc)(2)-mediated dehydrogenative aminoacyloxylation of β,γ-unsaturated hydrazones with Togni reagent II. The reaction is initiated by the carboxyl-containing species generated in situ from Togni reagent II, offering a new solution for regioselective functionalization at a remote site on β,γ-unsaturated hydrazones and providing a straightforward method for the synthesis of acyloxyl-substituted pyridazines. The reaction exhibits a broad substrate scope and can be carried out under mild conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
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)
