Review
Chemistry, Multidisciplinary
Piret Villo, Andrey Shatskiy, Markus D. Karkas, Helena Lundberg
Summary: Alcohols and their derivatives are commonly used in organic synthesis and their deoxygenative transformations are challenging due to the thermodynamic penalty of C-O bond cleavage. However, electrochemically driven redox reactions have been shown to facilitate this process through direct electron transfer or the use of electron transfer mediators and electroactive catalysts. This article provides a comprehensive overview of electrochemically mediated protocols for C-O bond activation and functionalization, including direct and indirect electrosynthetic methods, as well as photoelectrochemical strategies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Patricia C. Lin, Chetan Joshi, Tristan M. McGinnis, Sharath Chandra Mallojjala, Amberly B. Sanford, Jennifer S. Hirschi, Elizabeth R. Jarvo
Summary: A nickel-catalyzed cross-electrophile coupling reaction was developed for the synthesis of enantioenriched cyclopropane products containing vinyl fluoride substituents. The reaction involves the C-F bond activation of allylic gem-difluorides or the C-O bond activation of unactivated alkyl sulfonates. The findings of this study have significant implications in medicinal chemistry.
Article
Chemistry, Organic
Kensuke Kiyokawa, Ikumi Noguchi, Takaya Nagata, Satoshi Minakata
Summary: In this study, we present a bromocyanation reaction of styrene derivatives using cyanogen bromide in the presence of tris(pentafluorophenyl)borane as a Lewis acid catalyst. The reaction proceeds through a stereospecific syn-addition and provides a straightforward approach to beta-bromonitriles.
Article
Multidisciplinary Sciences
Kaluvu Balaraman, Christian Wolf
Summary: This study demonstrates the chemodivergent activation of monofluoroalkyl compounds towards either nucleophilic or electrophilic intermediates, expanding the scope of organofluorine chemistry and creating new synthetic opportunities for carbon-carbon and carbon-heteroatom bond formations.
Article
Chemistry, Multidisciplinary
Minghao Zhang, Zhiyang Ye, Wanxiang Zhao
Summary: We developed a cobalt-catalyzed remote borylation reaction for the enantioselective functionalization of alkyl halides, which provides a robust approach for the synthesis of chiral organoboronates. This method is compatible with primary, secondary, and tertiary bromides, allowing access to a broad range of alkylboronates. Moreover, the borylation of aryl halides was also demonstrated using this catalytic system. Preliminary mechanistic studies suggest a radical reaction pathway for this remote borylation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Lianyi Cao, Fangzhi Hu, Hongmei Sun, Xiaomei Zhang, Shuai-Shuai Li
Summary: A novel dearomative [5+1] annulation of 2-methylindoles with O-alkyl ortho-oxybenzaldehydes was developed, leading to the synthesis of spirochromanes bearing the 2-methylindolenine skeleton. Additionally, a dual alkylation of 2-methylindolenines was achieved through a redox neutral [5+1] annulation with N-alkyl ortho-aminobenzaldehyde. The study also demonstrated that the auxiliary group facilitating the hydride transfer process could be easily removed, further enhancing the synthetic efficiency.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yujuan Wang, Yiyang Cheng, Lei Zhong, Shuhui Lei, Yun He, Yuanwei Dai
Summary: A highly efficient palladium-catalyzed glycosylation reaction between 3,4-O-carbonate glycals and acid-labile oximes is described. This method offers a broad substrate scope, high functional group tolerance, and easy scalability, resulting in glycosyl oximes with excellent yields, exclusive β-selectivity, and retention of Z/E geometries. The versatility of this approach is demonstrated through site-selective transformations and late-stage glycodiversification of bioactive molecules. Overall, this strategy provides an efficient toolkit for accessing valuable N-O-linked glycosides.
Article
Chemistry, Organic
Hong Hu, Wen-Hua Xu, Wu-Xiang Kang, Wei Sun, Rui Sun, Xiao-Hong Wei, Meng Sun
Summary: An unprecedented Co(iii)-catalyzed stereoselective C-H homoallylation reaction has been developed for the synthesis of (E)-homoallylic alcohols from indole derivatives and 4-vinyl-1,3-dioxan-2-ones. This protocol offers mild reaction conditions, high efficiency, good yields, excellent stereoselectivity, and broad tolerance towards functional groups. It provides a powerful approach for the late-stage C-H homoallylation of bioactive and pharmaceutically relevant indole-based substrates.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Organic
Kevin George, Sathananthan Kannadasan
Summary: This review provides an overview of the synthetic utility of toluene and its derivatives, exploring the use of both alkyl-sp(3) and aryl-sp(2) carbons through C-H activation. The review also discusses the impact of different substituents on toluene derivatives in facilitating various reactions.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tuanli Yao, Rui Zhu, Tao Liu
Summary: In this study, a highly selective cyclocarboamination reaction was achieved using Zn(OTf)(2) as a catalyst, allowing for the synthesis of 3-aminoindenes with different substitution patterns. Furthermore, the complete reduction of iminoindenone intermediates led to the formation of cis-1-amino-2-arylindanes with excellent diastereoselectivity.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Tatsushi Yabuta, Masahiko Hayashi, Ryosuke Matsubara
Summary: The article reports a visible-light-induced photocatalytic cleavage method for alkyl aryl ether C-O bonds using a carbazole-based organic photocatalyst. Addition of Cs2CO3 is beneficial for the reaction, especially in reactions using a N-H carbazole organic photocatalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Guangning Ma, Samson Afewerki, Kaiheng Zhang, Ismail Ibrahem, Armando Cordova
Summary: The study demonstrates the ability of intermolecular cooperative thiourea/oxime hydrogen-bond catalysis to improve and accelerate asymmetric aminocatalysis by achieving highly stereoselective transformations through synergy.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Physical
Rahul Keshri, Debanjan Rana, Argha Saha, Shaeel Ahmed Al-Thabaiti, Abdulmohsen Ali Alshehri, Salem M. Bawaked, Debabrata Maiti
Summary: Transition-metal-catalyzed C(sp2)-H bond functionalization is a revolutionary strategy for efficient synthesis of complex heterocyclic frameworks. The use of free amine and alcohol as directing groups has shown significant advantages, allowing for the formation of C-C and C-heteroatom bonds and annulation cascades reactions. This review focuses on the utility of aromatic sp2-C-H functionalization directed by free amine and hydroxyl for constructing three to seven-membered N- and O-heterocycles.
Article
Chemistry, Organic
Bing Xu, Yang Ye, Ying Lin, Renren Bai, Xiang-Yang Ye, Tian Xie
Summary: In this study, we present a simple method for the plain manufacture of sterically hindered tertiary alkyl thioethers via the Cu-catalyzed coupling of unactivated tertiary alkyl alcohols with thio-alcohols/phenols. This method represents one of the most effective unactivated tertiary C (sp(3))-S bond-forming methods via readily accessible Lewis acid catalysis under easy-to-operate reaction conditions. Moreover, it has high functional group compatibility and wide substrate adaptability.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Hirokazu Moniwa, Masahiro Yamanaka, Ryo Shintani
Summary: Catalytic reactions involving metal migration from carbon to carbon provide a nonclassical approach to constructing organic molecular skeletons. In this study, a new and efficient synthesis of alkenylsilylmethylboronates was developed using copper catalysis, which proceeds regioselectively and involves an unprecedented alkenyl-to-alkyl copper migration.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(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)