Article
Chemistry, Organic
Sven C. Richter, Martin Oestreich
Summary: The chemoselective deoxygenation of secondary benzylic alcohols can be achieved through a series of formylation and reduction reactions, forming formates. In this process, the formyl group acts as both an activator and a self-sacrificing protecting group, allowing the reaction to proceed in the presence of other reducible groups.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jie Li, Xinhui Zhang, Yisen Yao, Yapei Gao, Wen Yang, Wanxiang Zhao
Summary: An efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reaction has been developed for the synthesis of oxygen atom-substituted allylboronates with aryl/vinyl bromides, iodides, and triflates. This protocol offers a broad substrate scope, excellent functional group tolerance, and easy gram-scale preparation, providing an alternative approach for the synthesis of allylic alcohols and their derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Adam Cook, Maxwell Bezaire, Stephen G. G. Newman
Summary: Herein, a protocol is disclosed that allows for the desulfonylative olefination of beta-hydroxy, beta-keto, and beta-ethereal sulfones using a Ni-NHC catalyst. This method enables the reliable synthesis of both nonconjugated and conjugated olefins with mono, di, tri, or tetrasubstitution patterns. A brief mechanistic exploration provides evidence for the presence of both radical and organonickel intermediates in the formation of the product.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Kieran Nicholson, Thomas Langer, Stephen P. Thomas
Summary: The use of stoichiometric organoborane reductants in organic synthesis has been well established. In this study, these reagents were rendered catalytic through an isodesmic B-O/B-H transborylation, enabling borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The proposed mechanism of catalysis involves 1,4-hydroboration and B-O/B-H transborylation as key steps, supported by single-turnover and isotopic labeling experiments.
Article
Chemistry, Multidisciplinary
Lanfeng Wei, Wenbo Bai, Zhiyan Hu, Zhiyong Yang, Liang Xu
Summary: The study developed a unified metal-free photooxidative platform for the cleavage of C-heteroatom bonds, using AQDAB complex as the photocatalyst to induce the oxidation process. This method allows for chemoselective cleavage of C-N, C-S, and C-Se bonds, broadening the potential applications of oxidation in synthetic chemistry. It established a photooxidation system for formal carbonylation of C-heteroatom (N, S, Se) bonds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Sobi Asako, Takafumi Kobayashi, Seina Ishihara, Kazuhiko Takai
Summary: A simple catalytic system composed of Mo(0) and ortho-quinone as catalyst, and phosphine as a reductant, has been developed for the synthesis of pyridoisoindoles and pyridoisoindolium salts through deoxygenation of carbonyl compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Johnny Z. Wang, Holt A. Sakai, David W. C. MacMillan
Summary: In this paper, a convenient catalytic method for the coupling of alcohols with alkenes under mild photocatalytic conditions using N-heterocyclic carbene (NHC)-mediated deoxygenative Giese-type addition is described. This method is applicable to a wide range of alcohol compounds and allows for late-stage diversification reactions, showing significant potential for various applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
John J. Monteith, Sophie A. L. Rousseaux
Summary: A Negishi cross-coupling method has been developed for the synthesis of alpha-aryl ester products using alpha-hydroxy ester derivatives and arylzinc reagents. This reaction is efficient, rapid, and mild, providing a complementary way of accessing desirable products.
Article
Chemistry, Organic
Aleksey Zerov, Irina A. Boyarskaya, Olesya Khoroshilova, Irina N. Lavrentieva, Alexander Slita, Ekaterina O. Sinegubova, Vladimir V. Zarubaev, Aleksander V. Vasilyev
Summary: Trimethylsilyl ethers of 1,5-diaryl-3-(trifluoromethyl)pent-1-en-4-yn-3-oles in the superacid TfOH give rise to reactive conjugated CF3-allylic-propargylic cations, which, in the presence of arenes and excess TfOH, lead to the formation of E-1,1,5-triaryl-3-(trifluoromethyl)-pent-2-en-4-ynes and CF3-bicyclic dihydroanthracene derivatives, respectively. These two main reaction pathways are dependent on the nucleophilicity of aryl substituents in CF3-pentenynes and external aromatic molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Joshua J. Clarke, Kevin Basemann, Neyen Romano, Stephen J. Lee, Michel R. Gagne
Summary: A novel diastereoselective, Lewis acid catalyzed 1,6-difunctionalization reaction of galactose and mannose derivatives has been developed using sequential nucleophile additions. The formation of a 3,6-anhydrosugar intermediate was found to be crucial for the 1,6-site-selectivity, and the reactivity of starting materials was influenced by the differences in basicity and stereoelectronic stabilization. The nucleophilicity parameter values of Mayr helped in predicting the most suitable reaction conditions for specific nucleophiles.
Review
Chemistry, Multidisciplinary
Carles Lluna-Galan, Luis Izquierdo-Aranda, Rosa Adam, Jose R. Cabrero-Antonino
Summary: Research in the field of ether synthesis has made significant progress in recent years, particularly in the development of catalytic reductive alcohol etherifications using carbonyl-based compounds and CO2. Other related transformations, such as catalytic acetal/ketal-to-ether or ester-to-ether reductions, have also shown promising advancements.
Article
Chemistry, Multidisciplinary
Yunqing He, Wanli Nie, Ying Xue, Qishan Hu
Summary: A study on the mechanism of B(C6F5)(3) catalyzed imine reduction under stoichiometric water conditions revealed four novel pathways induced by (C6F5)(3)B-OH2, different from previous mechanisms. These pathways involve nucleophilic water or amine catalysis and explain the experimental results.
Article
Chemistry, Physical
Risto Savela, Nataliya D. Shcherban, Marko M. Melander, Igor Bezverkhyy, Irina L. Simakova, Otto Langvik, Ekaterina Kholkina, Tamara Schindler, Annabelle Krauss, Karoliina Honkala, Dmitry Yu Murzin, Reko Leino
Summary: Selective hydrogenation of unsaturated imines over heterogeneous catalysts, specifically with iridium on carbon nitrides and amphoteric metal oxides in toluene solvent, provides the best selectivity towards unsaturated amines. This study demonstrates a promising catalytic performance and chemoselectivity, which has not been reported before, under atmospheric hydrogen pressure and low temperatures.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Organic
Takahiro Soeta, Kota Kaneta, Yuichi Hatanaka, Tomonori Ida, Yutaka Ukaji
Summary: This paper discusses the N-heterocyclic carbene (NHC)-catalyzed redox monoacylation of 1,n-linear diols using alpha-benzoyloxyaldehydes, which resulted in moderate to good selectivities and chemical yields. The original NHC with a pyridine moiety played a crucial role in achieving good chemoselectivities, and a wide range of 1,n-linear diols were successfully applied in this reaction.
Article
Chemistry, Organic
Se Yeon Park, Jaehwan Kim, Haye Min Ko
Summary: An efficient chemoselective reduction of isatin derivatives has been achieved using B(C6F5)3 catalyst, benzyldimethylsilane, and H2O. Importantly, a small amount of water has been found to be a highly effective reaction promoter, reducing both the reaction time and temperature for the synthesis of indolin-3-ones. Furthermore, excellent deuterium incorporation has been achieved by catalytic alpha-deuteration of indolin-3-ones using B(C6F5)3 and D2O.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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)