Article
Chemistry, Multidisciplinary
Pinglu Zhang, Nobuya Tsuji, Jie Ouyang, Benjamin List
Summary: A novel catalytic asymmetric intramolecular hydroarylation using strong and confined IDPi Bronsted acid catalysts has been demonstrated, enabling efficient and highly enantioselective formation of quaternary stereogenic centers from aliphatic and aromatic olefins with indoles. This transformation has a broad substrate scope and can be further elaborated into bioactive molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Zhuo Wu, Zechen Wu, Xueliang Sun, Weixin Qi, Zhengyang Zhang, Yanghui Zhang
Summary: The study presents a Pd-catalyzed intramolecular coupling of inert C(sp(3))-H and C(sp(2))-H bonds, leading to the formation of organic compounds.
Article
Chemistry, Organic
Guodong Ju, Yalong Li, Yingsheng Zhao
Summary: Inexpensive and commercially available 2,4,6-triphenylpyrrolium tetrafluoroborate (TPT) is used as an organic photocatalyst for the nucleophilic aromatic substitution of unactivated fluoroarenes with pyrazole derivatives (SNAr) to form azole arenes. The use of organic photoredox catalysis enables the easy operation of this method under mild conditions. Various fluorinated aromatic compounds are suitable electrophiles for this transformation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Physical
Shidheshwar B. Ankade, Anand B. Shabade, Vineeta Soni, Benudhar Punji
Summary: This review summarizes the transition-metal-catalyzed alkylations of C-H bonds on various arenes and heteroarenes using unactivated alkyl halides until October 2020. The review is divided into two major sections based on the substrates utilized for alkylation: alkylation of arenes and alkylation of heteroarenes. Substantial progress has been made in direct alkylation using primary, secondary, and tertiary alkyl halides as well as methylation and fluoroalkylation.
Article
Chemistry, Organic
Shuxiong Han, Shuo He, Zhibin Huang, Yingsheng Zhao, Gong Chen
Summary: A metal-free method was developed for the construction of 3,3-dimethyl isoindolinones via radical-mediated intramolecular coupling of two C-H bonds of N,N-diisopropyl benzamides. The reactions exhibited moderate to high yield and excellent chemoselectivity. A reaction sequence involving the formation of an alkyl radical through oxidative cleavage of alkyl C-H bond and the formation of a lactam ring through intramolecular homolytic aromatic substitution was proposed.
Article
Chemistry, Organic
Pei Liu, Na Hao, Dong Yang, Lingyun Wan, Tianyi Wang, Tao Zhang, Rui Zhou, Xuefeng Cong, Jie Kong
Summary: An iron-enabled para-selective C-H silylation of benzamide derivatives has been reported as an efficient and general route for the synthesis of para-silicon functionalized benzamides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Applied
Alessandro Palmieri, Marino Petrini
Summary: The limited nucleophilic character and bidentate nature of unactivated nitroalkane anions make alkylation and allylation procedures troublesome. This review summarizes the most rewarding approaches, mainly based on metal-catalyzed processes involving purely ionic or mixed ionic-radical intermediates, that have been devised to overcome this limitation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Amrita Das, Naoto Chatani
Summary: The Rh-catalyzed C-H alkylation of benzylamine derivatives with unactivated 1-alkenes using a picolinamide directing group was reported. Aromatic acids led to high linear selectivity, while aliphatic acids favored branched alkylation products. Deuterium labeling experiments showed involvement of a Rh-carbene intermediate in linear product formation, with a different reaction pathway observed for branched products.
Article
Chemistry, Organic
Fei Wang, Shun-Yi Wang
Summary: The visible-light-promoted free radical cross-coupling method facilitates the efficient construction of unsymmetrical alkyl-alkyl selenide compounds under mild metal-free conditions, providing a green and simple approach with a wide substrate scope, high yields, and easy operation. Additionally, this strategy can also be applied for the efficient synthesis of aryl-alkyl selenides, heteroaryl-alkyl selenides, and aryl-alkyl sulfides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Chun-Ting Chou, Chun-Wei Lu, Bing-Syuan Wu, Cheng-Che Tsai
Summary: This paper describes the study on the kinetic resolution of racemic secondary alcohols (O-nucleophiles) via stereoselective intramolecular allylic substitution. The reaction was achieved by the synergistic catalysis of palladium and chiral phosphoric acid, yielding chiral cis-1,3-disubstituted 1,3-dihydroisobenzofurans with a selective factor of up to 60.9 and a diastereomeric ratio of up to 7.8:1. The application of this methodology in the asymmetric synthesis of a compound with antihistaminic activity was demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Xiao-Feng Wu
Summary: A new selectivity-reversed borocarbonylation reaction method has been studied, which successfully synthesizes beta-boryl ketones with complete regioselectivity under the cooperative action of palladium and copper catalysts.
Article
Chemistry, Multidisciplinary
Tao He, Guoqiang Wang, Peng-Wei Long, Sebastian Kemper, Elisabeth Irran, Hendrik F. T. Klare, Martin Oestreich
Summary: A trityl-cation-initiated annulation of benzyl-substituted vinylcyclopropanes with hydrosilanes has been reported, leading to the formation of new Si-C(sp(3)) and C(sp(2))-C(sp(3)) bonds through intramolecular reactions. The reaction mechanism proposed based on computations is in agreement with experimental observations, resulting in the formation of unprecedented silicon-containing fused ring systems. Another tricycle with a 6/6/6 ring fusion structure was obtained from a phenethyl-substituted VCP derivative through a related but different reaction pathway.
Article
Chemistry, Physical
Tingting Sun, Jintong Zhang, Yijun Fang, Yu Zhou, Haiqun Cao, Gen Luo, Zhi-Chao Cao
Summary: Despite the challenge in selectively substituting an unactivated C-O bond, this study achieved enantioselective alkylative activation using a chiral nickel catalyst. The use of THF as a solvent facilitated the transformation by suppressing beta-H elimination. DFT calculations revealed the crucial role of THF coordination to Mg(II) in preventing beta-H elimination during reductive elimination.
Article
Chemistry, Multidisciplinary
Bin Sun, Rongcheng Shi, Kesheng Zhang, Xiaoli Tang, Xiayue Shi, Jiayun Xu, Jin Yang, Can Jin
Summary: A novel and green strategy for the synthesis of acylated quinazolinone derivatives has been developed, using a photo-induced decarboxylative cascade radical acylation/cyclization reaction. The reaction proceeds smoothly without the need for external photocatalysts, additives, or oxidants, and can be easily scaled-up under flow conditions with sunlight irradiation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Sapna Gahlot, Alessandro Gradone, Myriam Roy, Michel Giorgi, Simone Conti, Paola Ceroni, Marco Villa, Marc Gingras
Summary: The synthesis of regioisomeric asterisks containing a benzene core and naphthylthio arms was reported to study the properties of all-organic phosphors. Through sulfur component exchange reactions, non-phosphorescent materials can be converted into highly phosphorescent materials.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
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)