Review
Chemistry, Organic
Ani Deepthi, C. B. C. Meenakshy, Maneesh Mohan
Summary: This review discusses the use of donor-acceptor cyclopropanes (DACs) for building heterocycles. The generation of heterocycles from DACs can be achieved through (3+2), (3+3), and (4+3) cycloaddition pathways, as well as nucleophilic ring-opening reactions, intramolecular transformations, and cycloisomerizations with suitable catalysts. The mild reaction conditions and the wide range of starting materials make the DAC route attractive for heterocycle synthesis. The literature covered in this review spans from 2018 to 2023.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Rasma Kronkalne, Rudolfs Belaunieks, Artjoms Ubaidullajevs, Anatoly Mishnev, Maris Turks
Summary: A method was developed to produce five-membered heterocycles containing a trisubstituted olefin side chain through a 1,2-silyl shift reaction of Propargyl silanes and subsequent reactions with various nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Anu Jacob, Peter G. G. Jones, Daniel B. B. Werz
Summary: A new method for synthesizing tetrahydroselenophenes with exocyclic double bonds was reported, which involves the reaction of donor-acceptor cyclopropanes (DACs) with lithium alkynylselenolates in the presence of In(OTf)3. The method has a broad substrate scope and high yields.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Prasoon Raj Singh, Pratibha Kalaramna, Shamsad Ali, Avijit Goswami
Summary: A simple protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition reaction using SnCl4 as a Lewis acid catalyst. Good chemoselectivity was observed when DACs were treated, indicating that thiocyanate is more reactive than nitrile moiety in such reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Murugesan Thangamani, Kannupal Srinivasan
Summary: This method utilizes aroyl-substituted donor-acceptor (D-A) cyclopropanes and 1-naphthylamines as substrates, leading to the synthesis of dibenzo[c,h]acridines through nucleophilic ring-opening and subsequent fragmentation and cyclization reactions with reasonable substrate scope and 50-70% yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Siyeon Jeong, Jung Min Joo
Summary: The regiodivergent, non-directed C-H functionalization of five-membered heteroarenes with alkenes and alkynes has been successfully achieved, allowing systematic diversification of common structural cores. A carefully devised transition metal catalytic system and a judicious choice of metals, ligands, acid and base additives, and solvents are critical for achieving high selectivity in these reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Inorganic & Nuclear
Kevin Breitwieser, Peter Chen
Summary: The diverted Heck reaction is an effective method for synthesizing cyclopropanes not limited to three-membered rings but also extended to five-membered rings. Further investigation and optimization of boron and tin-based substrates have been carried out.
Article
Chemistry, Multidisciplinary
Quoc Hoang Pham, Andrew J. Tague, Christopher Richardson, Michael G. Gardiner, Stephen G. Pyne, Christopher J. T. Hyland
Summary: A Pd-catalysed (3 + 2) cycloaddition reaction of bis(trifluoroethyl) 2-vinyl-cyclopropane-1,1-dicarboxylate (VCP) with cyclic sulfamidate imine-derived 1-azadienes (SDAs) has been developed, leading to highly functionalized spiroheterocycles with three contiguous stereocentres, including a tetrasubstituted carbon bearing an oxygen functionality. The geminal trifluoroethyl ester groups can be selectively manipulated to afford spirocycles with four contiguous stereocentres. Additionally, reduction of the imine moiety can introduce a fourth stereocentre and expose a 1,2-amino alcohol functionality.
Article
Chemistry, Organic
Grzegorz Mloston, Mateusz Kowalczyk, Andre U. Augustin, Peter G. Jones, Daniel B. Werz
Summary: The reactivity of donor-acceptor cyclopropanes towards thioketenes was investigated, leading to the formation of exocyclic thioenol ethers in moderate to good yields in a (3+2)-cycloaddition using Sc(OTf)(3) as a Lewis acidic catalyst. Unsymmetrical thioketenes provided E/Z mixtures at the double bond, with the Z isomer being preferred.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Liangliang Yang, Haiyang Wang, Ming Lang, Shiyong Peng
Summary: This short review summarizes the recent impressive developments on the high-order dipolar annulations of donor-acceptor cyclopropanes and cyclobutanes to afford medium-sized (hetero)cycles.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
D. A. Denisov, R. A. Novikov, Yu. V. Tomilov
Summary: The diastereoselective synthesis of donor-acceptor bicyclopropyl, 8-phenyldispiro[2.3.2.0]-nonane-1,1-dicarboxylate, was successfully achieved, utilizing Lewis acids as synthetic equivalents of cis-1,6-zwitterionic intermediates. Different cyclization reactions were observed depending on the presence of GaCl3 or EtAlCl2, showcasing the versatile reactivity of the compound under different conditions. Additionally, the reaction with 4-phenyl-1,2,4-triazoline-3,5-dione in the presence of Yb(OTf)(3) resulted in the formation of an eight-membered heterocycle through an ionic [6+2] cycloaddition.
RUSSIAN CHEMICAL BULLETIN
(2021)
Article
Chemistry, Multidisciplinary
Qiyao Li, Junyi Gong, Ying Li, Ruoyao Zhang, Haoran Wang, Jianquan Zhang, He Yan, Jacky W. Y. Lam, Herman H. Y. Sung, Ian D. Williams, Ryan T. K. Kwok, Min-Hui Li, Jianguo Wang, Ben Zhong Tang
Summary: This study introduces a novel synthetic method to construct five-membered heterocyclic compounds with AIE characteristics under mild conditions, and achieves significant progress in cancer cell recognition and fluorescent patterning through a light-driven amplification strategy.
Article
Chemistry, Inorganic & Nuclear
Song-Shan Dai, Li Yang, Lin Zhou, YuanYuan Gao, Ran Fang, Alexander M. Kirillov, Lizi Yang
Summary: This study investigates the mechanism and control factors of Ga-based mediators in reactions through DFT calculations and analysis. The results reveal the key mediator and the factors influencing regioselectivity and chemoselectivity, providing insights for analyzing various Ga-mediated reactions.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Yan Wang, Li-Ming Zhao
Summary: We have disclosed a simple and general method for the synthesis of chromendiones through Rh(III)-catalyzed C-H functionalization/annulation reactions of nitrones with cyclic 2-diazo-1,3-diones by using nitrones as a traceless directing group. This method shows high efficiency and wide functional group compatibility. The derivatization of these chromendiones has also been demonstrated to enhance the synthetic utility of the transformation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Usman Nazeer, Aqsa Mushtaq, Ameer Fawad Zahoor, Freeha Hafeez, Irum Shahzadi, Rabia Akhtar
Summary: Cyclopropanes are valuable in heterocyclic chemistry for their reactivity. The Cloke-Wilson rearrangement of activated cyclopropanes is an efficient approach to synthesize oxygen, nitrogen, and sulfur-containing heterocyclic compounds. This rearrangement has been developed into a versatile method with high selectivity. Recent advances in Cloke-Wilson rearrangement have focused on synthesizing five-membered heterocycles and its application in natural product synthesis.
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)