Article
Chemistry, Applied
Deyuan Meng, Jing He, Woojin Yoon, Hoseop Yun, Jung Tae Han, Jaesook Yun
Summary: In this study, the catalytic 1,6-addition of chiral alkyl copper nucleophiles generated from borylalkenes and a copper-hydride catalyst was successfully conducted under mild conditions. The controlled chemo- and stereoselectivity played a crucial role in the reductive coupling process, resulting in efficient synthesis of asymmetric 1,6-adducts of p-quinone methides through multicomponent and catalytic tandem reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Lei Xie, Xuyang Zang, Wanxing Liu, Ping Wu, Zhaoxue Wang, Chenyi Zhao, Zhenzhen Gao, Xiaojing Li, Shaozhen Nie, Lingang Wu
Summary: An efficient method for the synthesis of a variety of large diarylmethane thioether derivatives is developed through catalyst-free 1,6-conjugate addition. The reaction yields high to excellent results, and the system is also suitable for other sulfur-based nucleophiles. The resulting products can be readily converted into other valuable diarylmethane derivatives.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Julien Escudero, Pieter Mampuys, Carl Mensch, Charles B. Bheeter, Robby Vroemans, Romano V. A. Orru, Jeremy Harvey, Bert U. W. Maes
Summary: o-Phenylene N-substituted iminocarbonates can be obtained through aerobic Ni-catalyzed reaction of readily available catechols and isocyanides. The choice of oxidant and absence of base are crucial to avoid unwanted catechol oxidation. This method is generally applicable to other oxidation-sensitive aromatic 1,2-bisnucleophiles, providing a new approach to important bicyclic heterocycles.
Article
Chemistry, Applied
Ting Zhou, Yuqi Zhu, Hong Zhang, Jieyin He, Hongguang Li, Ming Lang, Jian Wang, Shiyong Peng
Summary: A one-pot tandem annulation of 1,6-allenynes with organic azides was reported using copper catalysis and TsOH promotion, providing N-allyl 1,2,3-triazole-fused structures in moderate to excellent yields under mild reaction conditions. Additionally, the N-allyl products can be further diversified by selectively reducing them to the N-alkyl counterparts.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Cong Luo, Wen-hua Lu, Guo-qin Wang, Zheng-bing Zhang, Hai-qiong Li, Pan Han, Dan Yang, Lin-hai Jing, Chen Wang
Summary: A novel photocatalytic method for the preparation of diarylmethyl silanes was reported through silyl radicals addition strategy to p-QMs. The method could tolerate a variety of functional groups and provide moderate to excellent yields. The resulting silylation products could be easily converted into a series of bioactive GPR40 agonists and useful p-QMs precursors for the synthesis of compounds possessing both quaternary carbon centers and silicon substituents through simple operation. A plausible mechanism of silyl radicals to p-QMs was proposed based on experimental results and previous literature.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Erandi Liyanage Perera, Daesung Lee
Summary: In this study, a sequential inter- and intramolecular addition reaction on electron-deficient 1,3-diynes conjugated with a ketone, ester, or imide functionality is described. This process is effectively directed by a propargylic -OH or -NH functionality. Alcohols, amines, and thiols show excellent reactivity for the initial addition. The addition of amines occurs at ambient temperature, whereas other nucleophiles require high temperatures and a base additive.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Biochemistry & Molecular Biology
Jian-Qiang Zhao, Wen-Jie Wang, Shun Zhou, Qi-Lin Xiao, Xi-Sha Xue, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/aza-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments.
Article
Chemistry, Multidisciplinary
Emma Naulin, Marine Lombard, Vincent Gandon, Pascal Retailleau, Elsa Van Elslande, Luc Neuville, Geraldine Masson
Summary: This study reports a method for selectively controlling the regioselectivity of conjugated trienes and synthesizing chiral cis-3,6-dihydro-2H-1,2-oxazines. Modular access to three different regioisomers is achieved, and the utility of each regioisomeric cycloadduct is highlighted.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Rui-Qiang Jiao, Ya-Nan Ding, Ming Li, Wei-Yu Shi, Xi Chen, Zhe Zhang, Wan-Xu Wei, Xue-Song Li, Xiao-Ping Gong, Yu-Yong Luan, Xue-Yuan Liu, Yong-Min Liang
Summary: A glycoarylation reaction of activated olefins under visible-light irradiation has been achieved. Glycosyl radicals are generated by radical transfer strategies involving (TMS)(3)SiOH and glycosyl bromides. Subsequent radical translocation and rapid 1,4-aryl migration lead to the formation of β-sugaramide derivatives, and this reaction is compatible with eight types of sugars. Furthermore, the cascade reaction affords a quaternary carbon center with good functional group adaptability and high regioselectivity under mild conditions.
Article
Chemistry, Multidisciplinary
Qi Xia, Yaxuan Zhou, Xiaoning Yang, Yanqiu Zhang, Jiayi Wang, Gonghua Song
Summary: An efficient copper-catalyzed regioselective addition reaction of quinones with boronic acids, which enables the synthesis of various quinols and 4-phenoxyphenols, has been developed. The reaction is facilitated by a simple solvent exchange between H2O and MeOH and offers mild reaction conditions, easy operation, broad substrate scope, and excellent regioselectivity. Gram-scale reactions and further transformations of the addition products were also successfully explored.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Juntao Yang, Bingxian Liu, Junbiao Chang
Summary: A ruthenium(II)-catalyzed one-pot synthesis of highly substituted 1,2-dihydropyridines (DHPs) via a three component reaction system has been successfully developed. The reaction utilizes a simple Ru(II) catalyst without the need for specific ligands. The catalytic system shows excellent functional group compatibility with a wide range of starting materials. The obtained DHPs can be easily converted into tetrahydropyridines and azabicyclo[4.2.0]octa-4,7-dienes by subsequent reduction or [2 + 2] cycloaddition reaction.
Article
Chemistry, Multidisciplinary
Maria Jesus Cabrera-Afonso, Anasheh Sookezian, Shorouk O. Badir, Mirna El Khatib, Gary A. Molander
Summary: The study reports an intermolecular 1,2-dicarbofunctionalization using alkyl N-(acyloxy)phthalimide redox-active esters and organotrifluoroborates, which proceeds through a photochemical radical/polar crossover to achieve carboallylation, carboalkenylation, carboalkynylation, and carboarylation of alkenes with regio- and chemoselective control. The mechanistic intricacies were elucidated through Stern-Volmer quenching studies, photochemical quantum yield measurements, and trapping experiments of radical and ionic intermediates.
Article
Chemistry, Organic
Chada Raji Reddy, Ankita Kumari, Suraj Aswale, Amol D. Patil, Y. Lakshmi Prapurna
Summary: The reaction of alkynyl p-quinone methide (pQM) with keto-methylenes through a base-mediated tandem 1,6-addition/annulation sequence, [2 + 3] annulation, affords furans for the first time. Various functionalized furans, including fused derivatives, can be obtained in good to excellent yields under mild reaction conditions. The effectiveness of alkynyl pQMs is demonstrated by their ability to access isoxazoles, pyrazoles via [3 + 2] annulation, and pyridines through [3 + 3] annulation in the presence of different bis-nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Qingfa Tan, Ning Guo, Linhan Yang, Fei Wang, Xiaoming Feng, Xiaohua Liu
Summary: Pudovik addition/[1,2]-phospha-Brook rearrangement is an effective method for generating anionic nucleophiles and constructing C-C bonds in organic synthesis. In this study, we report the organocatalytic 1,6-conjugate addition of para-quinone methides using Pudovik addition/[1,2]-phospha-Brook rearrangement. The three-component reaction, catalyzed by a chiral guanidine-sulfonamide, showed high yields and excellent diastereo- and enantioselectivities, leading to biologically active oxindole/biaryl/phosphorus-based structures. A possible bifunctional catalytic mode was proposed to explain the chiral control of this process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zoe Beato, Xiangming Zhu
Summary: A new method for synthesizing superarmed thioglycosides via the ring opening of 1,2-orthoesters is reported, ensuring the necessary stereochemistry and using trimethylsilyl thioethers as sulfur nucleophiles to avoid the use of unpleasant free thiols.
Article
Chemistry, Organic
Tsuyoshi Mita, Hiroki Masutani, Sho Ishii, Yoshihiro Sato
Article
Chemistry, Multidisciplinary
Yoshihiro Oonishi, Shuichi Masusaki, Shunki Sakamoto, Yoshihiro Sato
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Koichi Katagiri, Haruka Kodera, Masanori Tayu, Nozomi Saito
Article
Chemistry, Applied
Tsuyoshi Mita, Masashi Uchiyama, Yoshihiro Sato
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Toshiki Akiyama, Yuki Wada, Makito Yamada, Yasunori Shio, Tetsuo Honma, Shuhei Shimoda, Kazuki Tsuruta, Yusuke Tamenori, Hitoshi Haneoka, Takeyuki Suzuki, Kazuo Harada, Hayato Tsurugi, Kazushi Mashima, Jun-ya Hasegawa, Yoshihiro Sato, Mitsuhiro Arisawa
Article
Chemistry, Physical
Ryohei Doi, Koji Shimizu, Yuma Ikemoto, Masashi Uchiyama, Mikiko Koshiba, Atsushi Furukawa, Katsumi Maenaka, Satoshi Watanabe, Yoshihiro Sato
Summary: This study reports a nickel-catalyzed cascade reaction to construct a 3-acylbenzo[b]furan skeleton. Through reaction condition optimization, the catalyst loading could be reduced to 5-10 mol %, leading to the synthesis of various functionalized compounds. Stoichiometric study of nickel complexes and DFT calculations were conducted to support a possible reaction mechanism.
Article
Chemistry, Multidisciplinary
Ryohei Doi, Kanako Hayashi, Yoshihiro Sato
Summary: In this study, palladium-catalyzed decarboxylative alpha-polyfluoroarylation of ketones was reported. By screening reaction conditions, XPhos and Ruphos were selected as ancillary ligands for Pd(0) catalysts, enabling the reaction to be applied to various substrates. A cross-over experiment was conducted to gain insight into the reaction mechanism.
Article
Chemistry, Organic
Yoshihiro Oonishi, Shunki Sakamoto, Shuya Agata, Yoshihiro Sato
Summary: In the Rhodium(I)-catalyzed enantioselective cyclization of enynes, the presence of different functional groups on the substrate molecules affects the structure and yield of the products, with C(sp(3))-H bond activation being an important high energy barrier step in the cyclization reaction.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Souta Misawa, Asaki Miyairi, Yoshihiro Oonishi, Steven P. Nolan, Yoshihiro Sato
Summary: Polarized alkynes such as ynol ethers and ynamides undergo Au(I)-catalyzed hydroalkoxylation/Claisen rearrangement cascade reactions with allylic alcohols, proceeding under mild conditions with high regioselectivity. The resulting gamma,delta-unsaturated esters or amides are formed in an atom-economical manner using the [Au(IPr)NTf(2)] catalyst.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Applied
Yoshihiro Oonishi, Kazuki Takagishi, Yi-Min Liu, Yoshihiro Sato
Summary: This article describes the rhodium-catalyzed enantioselective hydroacylation of racemic alkynals with a substituent at the alpha-position of the carbonyl group. The reaction can be applied to a wide range of substrates (22 examples), and mechanistic studies reveal a dynamic kinetic resolution (DKR) process during the hydroacylation, leading to various cyclic ketones with yields of 47-93% and enantiomeric ratios (er) of 59:41 to 97:3 from racemic starting materials.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Koji Yamada, Kaho Ishizawa, Yoshihiro Oonishi, Yoshihiro Sato, Takahide Nishi
Summary: This study presents a practical synthetic method for accessing oxazolidinone-2,3-fused indoline and azaindoline derivatives through one-pot cyclization. These derivatives, which contain sp3-hybridized carbons, could serve as novel scaffolds in medicinal chemistry.
Article
Chemistry, Organic
Mikiko Koshiba, Yuto Furuki, Kazuhiro Morisaki, Ryohei Doi, Yoshihiro Sato
Summary: We report a nickel-catalyzed migratory cycloisomerization reaction for the synthesis of 2,3-disubstituted indoles. The reaction proceeds via acyl transfer on the nitrogen atom of the substrate to the C3 position in the product, and a suitable N-heterocyclic carbene ligand is used in the reaction.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Asaki Miyairi, Yoshihiro Oonishi, Yoshihiro Sato
Summary: This study successfully demonstrated the one-pot synthesis of fully substituted 2-aminofurans via a gold-catalyzed cascade reaction, under highly mild conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Ryohei Doi, Yoshihiro Sato
NICKEL CATALYSIS IN ORGANIC SYNTHESIS: METHODS AND REACTIONS
(2020)
Meeting Abstract
Chemistry, Multidisciplinary
Toshiki Akiyama, Tetsuo Honma, Kazuki Tsuruta, Yusuke Tamenori, Yohei Ueda, Hayato Tsurugi, Kenichi Murai, Ohno Shohei, Kazushi Mashima, Hiromichi Fujioka, Yoshihiro Sato, Mitsuhiro Arisawa
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)
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)