Review
Chemistry, Organic
Nancy Slathia, Annah Gupta, Kamal K. Kapoor
Summary: The combination of molecular iodine and TBHP plays a significant role in organic synthesis and catalysis by enhancing the selectivity and sustainability of organic transformations. It can be utilized as a catalytic duo or as a reagent system with an additive, leading to metal-free and environmentally friendly protocols. This indispensable tool enables the formation of complex organic architectures through various reactions such as C-H functionalization, cyclization, cycloaddition, rearrangement, sulfonylation/sulfenylation, and oxidation reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guan-Jun Wang, Le Wang, Guo-Dong Zhu, Jia Zhou, He-Yuan Bai, Shu-Yu Zhang
Summary: This study describes an efficient method for the synthesis of chiral tetrahydroindole pyrazolinones through chiral phosphoric acid-catalyzed [3 + 2] cascade cyclizations, which exhibit a broad substrate scope, high yields, and excellent enantioselectivities. The research highlights the potential value of direct chiral indolizations from simple amine sources in organic synthesis.
Article
Chemistry, Multidisciplinary
Li Wang, Qi Zhong, Youliang Zou, Youzhi Yin, Aizhen Wu, Quan Chen, Ke Zhang, Jiachen Jiang, Mengzhen Zhao, Hua Zhang
Summary: Selective carbon-carbon bond activation was achieved through fragmentation borylation mediated by B(OMe)(3)/B(2)pin(2), leading to the formation of two C-B bonds in non-polar unstrained Csp(2)-Csp(3) and Csp(2)-Csp(2) bonds. This new reaction mode is expected to stimulate the development of reactions based on inert C-C bond activation, as suggested by preliminary mechanistic investigations.
Article
Chemistry, Multidisciplinary
Rahul A. Jagtap, Benudhar Punji
Summary: The paper summarizes the developments in nickel-catalyzed regioselective functionalization of azoles and indoles, with a particular focus on the reaction mechanism.
Article
Chemistry, Organic
Bingxu Han, Xuelu Ding, Yan Zhang, Xin Gu, Yunkun Qi, Shuai Liang
Summary: In this study, a Mn(OAc)3•2H2O promoted radical sulfonation reaction was reported, which achieved the construction of various heterocyclic fragments and the introduction of sulfonic moieties in one step. More than 50 heterocyclic sulfonates or their derivatives with different substituents were successfully synthesized with high efficiency under mild conditions.
Article
Chemistry, Multidisciplinary
Luca C. C. Greiner, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
Summary: In this study, phenyl azides substituted by an (alkylphenyl)ethynyl group were found to facilitate benzylic sp(3)(C-H) functionalization under the presence of a JohnPhosAu catalyst, resulting in the synthesis of indole-fused tetra- and pentacycles through divergent N- or C-cyclization. The chemoselectivity of the reaction was found to be influenced by the counter-anion, the electron density of the alpha-imino gold(I) carbene, and the alkyl groups stabilizing the benzylic carbocation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Junyu Chen, Tianshuo Zhong, Xiangyun Zheng, Chuanliu Yin, Lei Zhang, Jian Zhou, Xinpeng Jiang, Chuanming Yu
Summary: A novel method for the synthesis of fused tricyclic [1,3]oxazino[3,4-a]indol-1-ones and dihydropyrimido[1,6-a]indol-1(2H)-ones via Rh(III)-catalyzed [3+3] or [4+2] annulation of N-methoxy-1H-indole-1-carboxamides with sulfoxonium ylides has been successfully developed. The protocol features low catalyst loading and a broad substrate scope, providing the corresponding products in yields up to 99%.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Bingxu Han, Xin Gu, Ke Li, Yunkun Qi, Shuai Liang
Summary: In this study, we reported a previously unseen Mn-(OAc)3middot2H2O-promoted homolytic aromatic sulfonation. The reaction was carried out under mild conditions using K2S2O5 as a green sulfonating reagent, leading to high efficiency conversion of various arenes to desired sulfonic acids or sulfonates. Preliminary mechanistic studies revealed that the reaction proceeds via a homolytic aromatic substitution-type mechanism involving an SO3-radical, where the combination of Mn(OAc)3middot2H2O and HFIP plays a crucial role.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Subban Kathiravan, Prasad Anaspure
Summary: This paper reports an electrochemical intermolecular C-H/N-H oxidative annulation of 2-phenylpyrazoles with alkynes using a rhodium(iii) redox regime without external metal oxidants, in a water compatible solvent system. Both symmetrical and unsymmetrical alkynes were found to be compatible with the optimized conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xiao-Qing Song, Xiao-Qi Qiang, Zi-Jun Hu, Xinyu Lyu, Sheng Tan, Changsheng Yao, Yong-Qiang Sun, Chun-Bao Miao, Hai-Tao Yang
Summary: A concise method for the synthesis of 3-aryl-4-pyrrolin-2-ones was developed by copper-catalyzed [3+2] annulation of O-acyl ketoximes with 2-aryl malonates. The advantage of this method lies in the simultaneous generation of nucleophilic enamines and electrophilic p-quinone methides using O-acyl oximes as an internal oxidant. The subsequent nucleophilic addition selectively occurs on the a-C of malonates.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Peidong Xu, Weiwei Han, Yufeng Zhou, Heng-Ying Xiong, Shao-Fei Ni, Guangwu Zhang
Summary: A visible-light induced approach was developed to synthesize 3-alkyl indole from ynones via Csp(3)-H bond functionalization. This protocol proceeded under base-free conditions and at room temperature, providing a series of 3-alkyl indole motifs in yields ranging from 39% to 90% (44 examples). Preliminary mechanistic studies suggest the involvement of a radical process in this transformation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Diksha Parmar, Ankit Kumar Dhiman, Rohit Kumar, Akhilesh K. Sharma, Upendra Sharma
Summary: In this study, we report a Cp*Co(III)-catalyzed site-selective olefination and oxyarylation of quinoline N-oxides with terminal alkynes. The selectivity is controlled by steric hindrance and electronic factors.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Physical
Thaipparambil Aneeja, Mohan Neetha, C. M. A. Afsina, Gopinathan Anilkumar
Summary: Manganese-catalyzed C-H activation has rapidly become a powerful tool in organic synthesis, with high selectivity, eco-friendliness, and a wide substrate scope. This strategy has been widely applied in medicinal chemistry, materials science, and natural product synthesis, showing significant advances from 2018-2020.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Nathan P. Brites, Marina C. Dilelio, Ricardo F. Schumacher, Teodoro S. Kaufman, Claudio C. Silveira
Summary: A simple and robust coupling protocol is reported for the synthesis of previously unknown indole derivatives carrying vinylsulfide motifs attached to C-3 of the heterocycle. The strategy involved a Wittig-Horner reaction with different phosphinoxide derivatives, and the optimized reaction conditions were assessed for its scope and limitations. The target compounds were obtained in good to excellent yields as mixtures of geometric isomers.
Article
Chemistry, Organic
Yuanyuan Yue, Yan Yang, Chunying Sun, Junli Chao, Yaqing Ye, Xiaohui Guo, Jianming Liu
Summary: This study demonstrates the delivery of several polycyclic aromatic hydrocarbons through the copper-catalyzed aerobic oxidative C-H/C-H [4 + 2] annulation at room temperature, achieving dual aryl C-H functionalization. Mechanistic experiments show that the C-H bond cleavage on the indole and phenyl rings is not involved in the rate-limiting step.
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.