Article
Chemistry, Organic
Heng Zhang, Tianyun Guo, Mingzhong Wu, Xing Huo, Shouchu Tang, Xiaolei Wang, Jian Liu
Summary: A green photoredox oxidation method was reported for the conversion of benzylic primary and secondary alcohols to aldehydes and ketones using air as an oxidant. The oxidation exhibited broad substrate scope and excellent selectivity towards benzylic alcohols over aliphatic alcohols. Mechanistic studies revealed a quinuclidine mediated hydrogen atom transfer (HAT) process, along with blue LEDs promoting 4CzIPN photoredox cycle involved in the oxidation.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Yutaka Nishiyama, Shijie Xu, Yuuki Hanatani, Susumu Tsuda, Rui Umeda
Summary: The rhenium complex catalyzes the efficient reduction of benzylic, tertiary, and allylic alcohols using hydrosilane, resulting in the formation of alkanes. Different types of alcohols exhibit different side reactions.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Masatoshi Shibuya, Takayuki Orihashi, Yamei Li, Yoshihiko Yamamoto
Summary: The chemoselective benzylic C(sp(3))-H amination of unprotected arylalkanols catalyzed by N-hydroxyphthalimide has been successfully developed, with the critical role played by 1,1,1,3,3,3-hexafluoropropan-2-ol as a solvent. The conversion of the aminated product to the corresponding free amino alcohol was also demonstrated in this study.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Nuria Vazquez-Galinanes, Isabel Velo-Heleno, Martin Fananas-Mastral
Summary: A method for the use of vinyl epoxides in catalytic allylboration of alkynes is described, which allows for the synthesis of bifunctional skipped dienes bearing both an allylic alcohol and an alkenylboronate from simple starting materials with high regio- and stereoselectivity. These products show versatile reactivity and can be converted into cyclic boron compounds and polyenes.
Article
Chemistry, Multidisciplinary
Bowen Hu, Haoqiang Zhao, Yu Wu, Patrick J. Walsh
Summary: A novel, selective and high-yielding palladium-catalyzed carbonylative arylation of weakly acidic benzylic and heterobenzylic C(sp(3))-H bonds with aryl bromides has been achieved. The system allows access to diverse alpha-aryl or alpha,alpha-diaryl ketones, which are commonly found in biologically active compounds. The use of Josiphos SL-J001-1-based palladium catalyst enables the carbonylative arylation without the formation of direct coupling byproducts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Werner Oberhauser, Claudio Evangelisti, Laura Capozzoli, Gabriele Manca, Maria Pia Casaletto, Francesco Vizza
Summary: Palladium nanoparticles stabilized by a sterically demanding secondary diamine ligand were synthesized and used for catalyzing the aerobic oxidation of 1,2-propandiol. A selectivity switch induced by water was observed, while the stability of these nanoparticles under real catalytic conditions was demonstrated through recycling experiments and comparison with other types of palladium nanoparticles.
Article
Chemistry, Multidisciplinary
Jinshan Li, Wenxue Xi, Rong Zhong, Jianguo Yang, Lei Wang, Hanfeng Ding, Zhiming Wang
Summary: A novel method catalyzed by HFIP for the synthesis of various α,α-difluoroketones has been developed, which are important intermediates in medicinal and organic chemistry. Moreover, this method can also be applied in the late-stage dehydroxydifluoroalkylation of compounds.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Changhong Liu, Mamat Marhaba, Abdukerem Dilshat, Wenli Zhu, Kun Xia, Zechuan Mao, Abdukader Ablimit
Summary: This paper reports a nickel-catalyzed esterification reaction for the synthesis of mandelic acid esters with high yields. The reaction is conducted under mild reaction conditions and successfully utilized in the synthesis of medicine cyclandelate.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qiyuan He, Naoto Chatani
Summary: The palladium-catalyzed [3+2] annulation of aromatic amides with maleimides via the activation of ortho benzylic C-H and meta C-H bonds is reported, with a key role played by the presence of a 2-methylthiophenyl directing group for the success of the reaction. The irreversible cleavage of these C-H bonds leads to the formation of five-membered cyclic products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Jianyu Dong, Xiuling Chen, Fangyan Ji, Lixin Liu, Lebin Su, Min Mo, Jian-Sheng Tang, Yongbo Zhou
Summary: In the presence of copper salt and molecular oxygen, a simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved, resulting in a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, facilitating the oxygenation of C-H bond, cleavage of inert C-C bond, and formation of C-O bond in one pot without the need for any additional acids, bases, ligands, etc. This reaction provides a simple, direct, and efficient method for synthesizing functionalized esters, especially aryl benzoates, from readily available starting materials.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Estefania Tiburcio, Rossella Greco, Marta Mon, Jordi Ballesteros-Soberanas, Jesus Ferrando-Soria, Miguel Lopez-Haro, Juan Carlos Hernandez-Garrido, Judit Oliver-Meseguer, Carlo Marini, Mercedes Boronat, Donatella Armentano, Antonio Leyva-Perez, Emilio Pardo
Summary: Palladium single atoms can be spontaneously formed in neat benzyl alcohols and used for organic oxidation reactions without additives or solvents. By stabilizing Pd SACs within a metal-organic framework, a solid catalyst was successfully prepared and characterized.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Pit van Bonn, Daniela Dressler, Fabian Weitenhagen, Carsten Bolm
Summary: A mechanochemical palladium-catalyzed oxidative esterification of alcohols has been developed, enabling the solvent-free synthesis of esters with high yields. The environmental performance of the developed protocol was evaluated and compared with solution-based protocols, highlighting the advantages of the mechanochemical approach.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Kento Asai, Koji Hirano, Masahiro Miura
Summary: A new method for the palladium-catalyzed benzylic silylation of diarylmethyl carbonates with silylboranes has been developed. The reaction proceeds smoothly even without external base, and high yields of benzylic silanes are obtained. The obtained silanes can work as nucleophiles and react with carbon electrophiles to deliver benzylic C-C cross-coupled products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Amardeep Ramprasad Jadhao, Sanjay Subhash Gaikwad
Summary: A facile and sustainable copper-catalyzed thiolation method has been developed to efficiently construct benzylic thioethers under mild reaction conditions. This approach avoids the use of commonly employed thiolation reagents, making it an attractive method for benzylic thioether synthesis due to the commercial availability of base and reagents, broad substrate scope, and convenient reaction procedure.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Ruonan Ma, Zhiyin Xiao, Wei Zhong, Chunxin Lu, Zhongquan Shen, Dan Zhao, Xiaoming Liu
Summary: The study revealed that the rate of oxidation reaction depends on the formation rate of active species, and halides actively participate in the catalysis by coordinating to Cu(I) in the active species. The electron-withdrawing substituent benefits the oxidation process and can offset the steric effect of ortho-substituents.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xingfeng Bai, Caizhi Wu, Shaozhong Ge, Yixin Lu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Physical
Qing Wang, Fei Ye, Jian Cao, Zheng Xu, Zhan-Jiang Zheng, Li-Wen Xu
CATALYSIS COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Jun-Han Ma, Li Li, Yu-Li Sun, Zheng Xu, Xing-Feng Bai, Ke-Fang Yang, Jian Cao, Yu-Ming Cui, Guan-Wu Yin, Li-Wen Xu
SCIENCE CHINA-CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Zhao Li, Xu Wang, Yu-Ming Cui, Jun-Han Ma, Li-Lei Fang, Lu-Lu Han, Qin Yang, Zheng Xu, Li-Wen Xu
Summary: The study successfully combined palladium-catalyzed DKR with C-H functionalization to synthesize non-biaryl-atropisomer-type (NBA) axially chiral organosilanes, providing a new approach for the synthesis of multifunctional axially chiral organosilicon compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Xiao-Bing Chen, Li Li, Wan-Chun Yang, Kun-Long Song, Bin Wu, Wan-Er Gan, Jian Cao, Li-Wen Xu
Summary: In this study, a novel palladium-catalyzed C-C bond activation of methylenecyclobutanes followed by Suzuki cross-coupling reaction was reported, leading to the formation of multisubstituted indanes. The tandem reaction process involves intramolecular carbopalladation of double bond, beta-carbon elimination, and intermolecular trapping of the transient sigma-alkylpalladium complex with boronic acids. A new TADDOL-derived phosphoramidite ligand containing fluorine and silicon-based bulky groups was found to be efficient for C-C bond activation of methylenecyclobutanes.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Wan-Chun Yang, Xiao-Bing Chen, Kun-Long Song, Bin Wu, Wan-Er Gan, Zhan-Jiang Zheng, Jian Cao, Li-Wen Xu
Summary: This study demonstrated a palladium-catalyzed asymmetric tandem C-C bond activation/Cacchi reaction between cyclobutanones and o-ethynylanilines, leading to the synthesis of one-carbon-tethered chiral indanone-substituted indoles with multiple new bonds and stereocenters.
Article
Chemistry, Multidisciplinary
Jia-Le Xie, Zheng Xu, Han-Qi Zhou, Yi-Xue Nie, Jian Cao, Guan-Wu Yin, Jean-Philippe Bouillon, Li-Wen Xu
Summary: The study presents a highly enantioselective hydrosilylation of ynones using a palladium catalyst with a chiral ligand, leading to the formation of a series of silicon-stereogenic silylenones with high yield and enantioselectivity. The reaction mechanism and origin of high degree of stereoselectivity were elucidated through density functional theory calculations, highlighting the importance of aromatic interactions in the reaction.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Organic
Fei Ye, Li-Wen Xu
Summary: Silicon and its related organosilicon chemistry have become integral parts of synthetic chemistry due to their ability to participate in various organic transformations. The advances in catalytic hydrosilylation and synthesis of silicon-stereogenic silanes demonstrate the significance and potential of organosilicon chemistry in academic research and industrial applications.
Article
Chemistry, Multidisciplinary
Hui-Lin Li, Wei-Sheng Huang, Fang-Ying Ling, Li Li, Jun-Hao Yan, Hao Xu, Li-Wen Xu
Summary: Organosilicon compounds are important reagents and intermediates in the construction of new materials and complex products. In this study, a highly diastereoselective rhodium-catalyzed cycloisomerization reaction was demonstrated using (EtO)3SiH to accelerate the cyclization reaction and yield spiro-fused succinimide and pyrazolone derivatives as a single diastereoisomer. The proposed mechanism involves an active Rh-H species from the hydrosilane as the H-donor in the spiro-type cycloisomerization reaction.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Gilles De Smet, Xingfeng Bai, Carl Mensch, Sergey Sergeyev, Gwilherm Evano, Bert U. W. Maes
Summary: This study demonstrates that acetate can serve as a renewable leaving group for selective deoxygenation of phenolics. The Ni-catalyzed reaction in a green solvent allows for efficient deoxygenation without affecting specific functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kun-Long Song, Bin Wu, Wan-Er Gan, Wan-Chun Yang, Xiao-Bing Chen, Jian Cao, Li-Wen Xu
Summary: The palladium-catalyzed carbonylative C-C bond activation reaction described in this study involves C-C bond cleavage, ring-opening, and amino- or alkoxycarbonylation reactions on cyclobutanones. Two C-C bonds and one C-O or C-N bond are formed under gas-free conditions using CO surrogates, yielding a variety of indanones with ester or amide groups.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Qiu-Qi Mu, Yi-Xue Nie, Hang Li, Xing-Feng Bai, Xue-Wei Liu, Zheng Xu, Li-Wen Xu
Summary: This study achieved highly enantioselective kinetic resolution of sterically hindered benzylamines for the first time through transition-metal-catalyzed oxidative carbonylation, providing a new approach to chiral isoindolinones (er up to 97:3). The origin of chemoselectivity and stereoselectivity was confirmed by density functional theory (DFT) calculations.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Li Li, Yun-Long Wei, Li-Wen Xu
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
