Article
Chemistry, Multidisciplinary
Christopher J. J. Hall, William R. F. Goundry, Timothy J. Donohoe
Summary: Enantiopure 1,2-amino alcohols derived from abundant amino acids were used in C-C bond-forming hydrogen-borrowing alkylation reactions for the first time. The use of Ph*COMe aryl ketone facilitated the reactions, preventing racemisation of the amine stereocentre. The Ph* and trityl groups could be easily cleaved in one pot to give GABA products without further purification, allowing the two steps to be performed in sequence without isolation of the hydrogen-borrowing intermediate, eliminating the need for column chromatography.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Allwin D. McDonald, Samantha K. Bruffy, Aadhishre T. Kasat, Andrew R. Buller
Summary: In this study, we used a substrate multiplexed screening approach to improve the substrate scope overlap in biocatalytic cascades for the synthesis of chiral 1,2-amino alcohols. By engineering the activity of enzymes, we achieved selective and efficient synthesis of enantiopure products in a one-pot cascade reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Federica Valentini, Giulia Brufani, Gabriele Rossini, Filippo Campana, Daniela Lanari, Luigi Vaccaro
Summary: We have developed a waste minimization protocol for the azidation reaction of a,fi-unsaturated carbonyl compounds using TMSN3. By selecting the appropriate catalyst (POLITAG-M-F) and reaction medium, we achieved enhanced catalytic efficiency and reduced environmental impact. The use of the CH3CN:H2O azeotrope as the reaction medium and for the workup procedure allowed for easy product isolation with high yield and low waste generation.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Physical
Lyazid Ait Said, Mohamed Merouane El Hammoumi, Chaimaa El Haimer, Abdelhadi El Bachiri, Mostafa Khoukhi
Summary: Two new compounds of beta-amino alcohol were synthesized using (R)-(+)-alpha-methylbenzylamine as the starting material, and these compounds were found to react with a 1:1 mixture of cis and trans-limonene oxide in the presence of water, yielding beta-amino alcohols and unreacted limonene oxides or amines in the products.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Medicinal
Hayato Kanai, Kuniyo Yamada, Koichi Kodama, Yasuhiro Ishida
Summary: Chiral amphiphiles play an important role in controlling the structures and properties of supramolecular assemblies, but their synthesis has been challenging. Researchers have improved the synthesis efficiency of amphiphilic 1,2-amino alcohols (S)-1 and (1S,2S)-2 by developing new synthetic schemes, resulting in higher overall yields and reduced risk of optical isomerization.
Article
Chemistry, Organic
Dongmin Kwak, Sehwa Jung, Hyeonbin Ha, Taedong Han, Do Hyun Ryu, Hyunwoo Kim, Jaesung Kwak
Summary: We present efficient synthetic methods for 1,2-aminoalcohols via electroreductive coupling between N-acyl diarylketimines and aldehydes. Mechanistic studies suggest that the reaction is initiated by selective electrochemical single electron transfer (SET) of N-acylketimines. The developed electrochemical protocol is compatible with biorelevant functional groups, allowing late-stage functionalization of pharmacophores.
Article
Chemistry, Organic
Cai Gao, Jiahao Zeng, Xianming Zhang, Yanzhi Liu, Zhuang-Ping Zhan
Summary: We developed a new photo-sensitizer, 2,4,5,6-tetrakis(2,7-dibromo-9H-carbazol-9-yl)isophthalonitrile (2,7-Br-4CzIPN), for the energy-transfer-driven N-O bond dissociation of oxime esters. In the presence of 2,7-Br-4CzIPN, difunctionalization of alkenes with oxime esters, including oxyimination, amino-carboxylation, and amidylimination, could afford versatile molecules with good yields and excellent regioselectivity, which are commonly found in natural products and drugs. Theoretical investigations and experiments have confirmed that 2,7-Br-4CzIPN possesses unique photophysical properties, suitable triplet energy, and outstanding photocatalytic activity.
Article
Agricultural Engineering
Ming Ho To, Huaimin Wang, Yahui Miao, Guneet Kaur, Sophie L. K. W. Roelants, Carol Sze Ki Lin
Summary: Large scale food waste was analyzed to determine the concentration of potential inhibitors, and lactic acid, acetic acid, and ethanol were identified as inhibitors of the growth of S. bombicola and its SLs production. Various methods were evaluated to remove these inhibitors, and a simple and effective strategy for removing inhibitors from food waste was developed, complying with the 12 principles of green chemistry and suitable for industrial high SLs production.
BIORESOURCE TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Yu Li, Na Hu, Zefei Xu, Yunfeng Cui, Jinhui Feng, Peiyuan Yao, Qiaqing Wu, Dunming Zhu, Yanhe Ma
Summary: The enzymatic asymmetric reductive amination process can be used to convert simple aldehydes and amines into chiral N-substituted 1,2-amino alcohols, providing an environmentally friendly and economical method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Tianyi Zheng, Janna L. Berman, Forrest E. Michael
Summary: In this study, a diastereoconvergent synthesis of anti-1,2-amino alcohols bearing N-containing quaternary stereocenters was reported. By destroying the allylic stereocenter, a single diastereomer of the product can be selectively formed from any diastereomeric mixture of the starting homoallylic alcohol derivatives, eliminating the need for diastereoselective preparation of starting materials.
Review
Chemistry, Multidisciplinary
Anamika Sharma, Ashish Kumar, Beatriz G. de la Torre, Fernando Albericio
Summary: This review provides a comprehensive overview of liquid-phase peptide synthesis (LPPS) as the third wave for peptide synthesis, discussing its principles, advantages, and various tags and methods associated with LPPS.
Article
Chemistry, Organic
Si-Si Ning, Dan Meng, Jie-Yun Zhang, Shi-Lei Liu, Ni-Ni Zhou, Xiaojie Jin, Hai-Tao Zhu
Summary: A metal-free intramolecular [3+2] cycloaddtion of benzene-linked propynol-ynes in AcOH/H2O has provided a greener and more practical route to functionalized naphtho[1,2-c]furan-5-ones with high regioselectivity. Additionally, regioselective alpha-deuteration of the naphtho[1,2-c]furan-5-ones showed excellent deuterium incorporation and yields. The fluorescent properties of the naphtho[1,2-c]furan-5-one products were also investigated in solution.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Materials Science, Multidisciplinary
Yew Jin Ong, Sreekumar Pisharath, Yang Feng Anders See, Chor Yong Tay, Huey Hoon Hng
Summary: In this study, a novel hybrid oligomer BANFHOB was developed as an energetic plasticizer for a cast curable fluoropolymer binder. BANFHOB, containing fluoroalkyl and azido moieties, exhibited good plasticizing effects by imparting oxidizing and energy release properties.
JOURNAL OF MATERIALS RESEARCH
(2022)
Article
Computer Science, Information Systems
B. Mohinder Singh, Jaisankar Natarajan
Summary: In response to the Covid-19 pandemic, many countries are transitioning from paper-based health record management to digital systems. Digital health records offer the advantage of easy data sharing, but the security of sensitive health data is crucial for gaining stakeholders' trust. This paper proposes a novel secure authentication protocol for digitizing personal health records. The protocol utilizes asymmetric and quantum-resistant encryption algorithms to protect data during transmission and verifies user authenticity and citizenship. The analysis shows that the protocol provides better security, storage cost, and computation compared to existing protocols.
JOURNAL OF KING SAUD UNIVERSITY-COMPUTER AND INFORMATION SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Francesca Valentini, Pierluca Galloni, Diana Brancadoro, Valeria Conte, Federica Sabuzi
Summary: This study proposes a sustainable solvent-free acetylation reaction method, in which the naturally occurring phenol is converted to the corresponding ester with the presence of 1% of VOSO4 as catalyst. The method is not only applicable for the synthesis of other esters, but also for acetylation of alcohols and thiols, and a greener alternative, isopropenyl acetate, has been introduced for further improvement.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jose Osorio-Tejada, Francesco Ferlin, Luigi Vaccaro, Volker Hessel
Summary: This contribution focuses on the progress of synthesis methods for 2-aryl benzoxazoles and evaluates their environmental profile, finding that continuous-flow technology is superior in reducing environmental impact.
Article
Chemistry, Multidisciplinary
Minjeong Lee, Seungjae Yun, Dongil Ho, Taeshik Earmme, Assunta Marrocchi, Luigi Vaccaro, Choongik Kim
Summary: This study successfully demonstrated the use of sustainable green solvents in the fabrication of organic semiconductor devices, showing promising results in terms of device performance and transfer gain. The devices fabricated using green solvents exhibited typical ambipolar characteristics and decent transfer gain, indicating the potential application of green solvents in the manufacture of organic semiconductor devices.
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY
(2022)
Article
Chemistry, Organic
Di Hao, Zhen Yang, Yali Liu, Yang Li, Chuntian Li, Yanlong Gu, Luigi Vaccaro, Jichang Liu, Ping Liu
Summary: An efficient Pd-catalyzed direct C-H arylation of pyrrolo[1,2-a]quinoxalines with aryl iodides has been developed, providing a selective route to a series of 1-arylated and 1,3-diarylated pyrrolo[1,2-a]quinoxalines with good yields. The method features broad substrate scope, good functional group tolerance, and gram-scale synthesis capability. Additionally, C3-thiocyanation of the arylated product has been achieved, indicating potential applications in organic synthesis and medicinal chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Yang Li, Yali Liu, Di Hao, Chuntian Li, Yan Liu, Yanlong Gu, Luigi Vaccaro, Ping Liu
Summary: An efficient Cu(II)-catalyzed direct C-H trifluoromethylation of pyrrolo[1,2-a]quinoxalines with CF3SO2Na in the presence of K2S2O8 has been developed. The reaction provides a variety of C1-trifluoromethylated pyrrolo[1,2-a]quinoxaline products in moderate to good yields. This method demonstrates broad substrate scope, excellent regioselectivity, and gram-scale synthesis.
Article
Chemistry, Physical
Xuezhen Li, Jing He, Mingxi Du, Jie Zhang, Yanlong Gu, Luigi Vaccaro, Ping Liu
Summary: An efficient I-2/K2S2O8-promoted ring expansion of benzo[d]thiazole and 3-oxo-3-arylpropanenitrile was developed, yielding diverse 3-aryl-4H-benzo[b][1,4]thiazine-2-carbonitriles in moderate to excellent yields. The protocol is characterized by metal-free reaction conditions, stable starting materials, and good group tolerance. Mechanistic studies suggest the reaction may proceed via a free radical process.
MOLECULAR CATALYSIS
(2022)
Review
Chemistry, Physical
Federica Valentini, Assunta Marrocchi, Luigi Vaccaro
Summary: Liquid organic hydrogen carriers (LOHCs) are attractive materials that can generate hydrogen on site for the production of biofuel precursors, fuels, or fuel additives. This comprehensive review article provides an overview of the hydrogen transfer mechanisms for different LOHCs and discusses the importance of catalyst design and reaction condition selection.
ADVANCED ENERGY MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Nihad Salameh, Francesco Ferlin, Federica Valentini, Ioannis Anastasiou, Luigi Vaccaro
Summary: This article describes an effective synthetic protocol for the synthesis of oxindoles in flow based on a C(sp(3))-H activation process promoted by a supported N-heterocyclic carbene palladium heterogeneous catalytic system. The use of CPME as the reaction medium, along with the design of an efficient continuous flow reactor, has led to a waste-minimized intramolecular cyclization process.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Physical
Nihad Salameh, Ioannis Anastasiou, Francesco Ferlin, Francesco Minio, Shaomin Chen, Stefano Santoro, Ping Liu, Yanglong Gu, Luigi Vaccaro
Summary: This study presents a waste-minimized protocol for the synthesis of oxindoles using cyclopentyl methyl ether as the reaction medium and palladium on carbon as the reusable catalyst. The protocol demonstrates high efficiency, minimal metal contamination, and minimal waste production. The catalyst can be recovered and reused without any apparent loss of efficiency. The products can be isolated by simple precipitation and both the reaction medium and solvent can be recovered.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Federica Valentini, Giulia Brufani, Benedetta Di Erasmo, Luigi Vaccaro
Summary: The great challenge for modern research is to define efficient tools for more sustainable industrial production and manufacturing. One aspect that requires attention is the replacement of toxic and non-renewable solvents. This contribution highlights the benefits of using gamma-valerolactone (GVL) as a circular, safe, biomass-derived reaction medium, covering recent publications (2021).
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2022)
Article
Chemistry, Organic
Tian Sang, Chuntian Li, Fan Jia, Jing He, Yan Liu, Luigi Vaccaro, Jichang Liu, Ping Liu
Summary: This study has developed a series of halogenated systems for pyrazolo[1,5-a]pyrimidines, achieving selective transformations by mono- and di-iodination using varying ratios of pyrazolo[1,5-a]pyrimidines and NIS. Additionally, the reaction with NBS or NCS produces unique dibrominated or dichlorinated products. The wide range of substrates, good functional group tolerance, and gram-scale synthesis demonstrate the potential application of this reaction.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Review
Chemistry, Physical
Federica Valentini, Oriana Piermatti, Luigi Vaccaro
Summary: The direct functionalization of inactivated C-H bonds has gained attention as a method for step-economy, atom-efficient, and environmentally sustainable processes. The design and preparation of highly active metal nanoparticles as catalysts for C-H bond activation under mild reaction conditions is still being investigated. This review focuses on the functionalization of un-activated C(sp3)-H, C(sp2)-H, and C(sp)-H bonds using metal and metal oxide nanoparticles for C-O and C-X (X = Halogen, B, P, S, Se) bond formation, leading to more sustainable access to industrial production.
Review
Chemistry, Multidisciplinary
Dario Marchionni, Sumon Basak, Alireza Nazari Khodadadi, Assunta Marrocchi, Luigi Vaccaro
Summary: The past decade has witnessed a renewed interest in borazines and BN-doped polycyclic aromatic hydrocarbons due to their potential in various applications. This review critically examines the synthesis methods of (substituted) B3N3 motifs and focuses on the discussion of borazine-doped carbon structures developed for materials science applications.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Nihad Salameh, Federica Valentini, Olivier Baudoin, Luigi Vaccaro
Summary: We report a general and efficient enantioselective C-H arylation of aryl bromides using BozPhos as the bisphosphine ligand and SP-NHC-PdII as recoverable heterogeneous catalyst. By exploiting the release and catch mechanism of action, high enantioselectivities were achieved across different substrates containing methyl, cyclopropyl and aryl C-H bonds. The developed catalytic system provides a more sustainable solution for the synthesis of high added-value chiral products through recycling of the precious metal.
Article
Chemistry, Multidisciplinary
Giulia Brufani, Federica Valentini, Gabriele Rossini, Lucia Rosignoli, Yanlong Gu, Ping Liu, Luigi Vaccaro
Summary: Metal contamination is a significant problem in chemical synthesis, especially for products with biological activity. The use of appropriate operating conditions, such as a copper tube flow reactor (CTFR), can greatly reduce metal leaching and waste generation. A waste-minimized continuous flow process for synthesizing 1,4-disubstituted β-keto 1,2,3-triazoles was developed, which demonstrated low environmental impact through the measurement of various green metrics.
GREEN SYNTHESIS AND CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jose Luis Osorio-Tejada, Francesco Ferlin, Luigi Vaccaro, Volker Hessel
Summary: Carbon-to-carbon (C-C) cross-coupling reaction (CCR) protocols are a major breakthrough in synthetic chemistry, widely used in medicinal chemistry and other applied sciences. This study uses life cycle assessment (LCA) to evaluate the environmental impact of CCRs, separating intrinsic and extrinsic impacts. The findings suggest the need to recycle the catalyst, carefully choose the halobenzene, and recycle the ligand along with the catalyst.
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.
