Default Latest Most Read Please wait a minute... Articles Electrochemical Synthesis of Tetrasubstituted Hydrazines by Dehydrogenative N-N Bond Formation Feng Enqi, Hou Zhongwei, Xu Haichao Chin. J. Org. Chem. 2019, 39 (5): 1424-1428. DOI: 10.6023/cjoc201812007 Published: 18 January 2019 Abstract (538) PDF (414KB)(571) Knowledge map An electrochemical synthesis of tetrasubstituted hydrazines through dehydrogenative dimerization of secondary amines has been developed. The reactions are conducted in a simple undivided cell with constant current. The use of electricity to promote the reactions obviates the need for transition metal catalysts and oxidizing reagents, providing an efficient and sustainable access to tetrasubstituted hydrazines with diverse electronic properties. Reference | Supporting Info. | Related Articles | Metrics ARTICLE Paired Electro-synthesis of Aryl Nitriles Cao Zhicheng, Liu Jianchao, Chu Youqun, Zhao Fengming, Zhu Yinghong, She Yuanbin Chin. J. Org. Chem. 2019, 39 (9): 2499-2506. DOI: 10.6023/cjoc201903052 Published: 15 May 2019 Abstract (186) PDF (639KB)(314) Knowledge map The electro-oxidation cyanation of p-methoxybenzyl alcohol (p-MeOC6H4CH2OH) to prepare aryl nitriles was studied by using cyclic voltammetry (CV) and constant current electrolysis (CCE). The effects of the volume ratio of H2O, concentration of H2SO4, temperature, electrode materials, current density and solvents on the electro-chemical reaction were studied. The results showed that the yield of p-methoxylbenzonitrile (p-MeOBN) was 90% in 0.15 mol·L-1 H2SO4 and 30% H2O-DMSO solution at 60℃ and 10 mA/cm2 of current density when tetrabutylammonium perchlorate (Bu4NClO4) was used as electrolyte. The CCE of aromatic benzyl alcohols with different p-and o-substituted analogs was investigated under the optimized reaction conditions, and the yields toward formation of the corresponding aryl nitriles were 61%~92%. A plausible mechanism for the electro-oxidation cyanation procedure was proposed. A novel paired electrochemical method for the synthesis of aryl nitriles from aromatic benzyl alcohols with hydroxylamine (HAM) as "N" source and aldehyde in situ in undivided electrochemical cell was successfully developed. Reference | Supporting Info. | Related Articles | Metrics Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization for the Synthesis of α-Pyrones Ye Zenghui, Zhang Fengzhi Chinese Journal of Organic Chemistry 2020, 40 (1): 241-242. DOI: 10.6023/cjoc202000002 Abstract (170) PDF (425KB)(382) Knowledge map Reference | Related Articles | Metrics Zinc-Catalyzed Asymmetric 6π Electrocyclization of Isoxazoles and Enynol Ethers Ou Pengcheng, Huang Xueliang Chinese Journal of Organic Chemistry 2020, 40 (4): 1074-1075. DOI: 10.6023/cjoc202000016 Abstract (160) PDF (406KB)(135) Knowledge map Reference | Related Articles | Metrics Electrocatalytic Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles Li Mengfan, Wang Rong, Hao Wenjuan, Jiang Bo Chinese Journal of Organic Chemistry 2020, 40 (6): 1540-1548. DOI: 10.6023/cjoc202002029 Published: 10 April 2020 Abstract (214) PDF (572KB)(403) Knowledge map 1,3,4-Oxadiazoles, standing for a class of five-membered heterocyclic compounds with multiple heteroatoms, show anti-inflammatory, anti-convulsant, anti-inositol and other biological activities. They also served as important intermediates in organic synthesis. Thus, the development of general and straightforward methods for their synthesis is of great significance. In this paper one-step synthesis of non-symmetric 2,5-disubstituted 1,3,4-oxadiazole derivatives with good yield was completed under electrocatalytic conditions by using cheap and readily available aldehydes and hydrazides as starting materials. Their structures were confirmed by IR, 1H NMR, 13C NMR and HRMS analyses. The reaction features mild conditions, high atom-economy and wide substrate scope, providing a green and sustainable synthetic protocol for constructing 1,3,4-oxadiazole skeleton. Reference | Supporting Info. | Related Articles | Metrics Advances in Asymmetric Organotransition Metal-Catalyzed Electrochemistry Wang Xiangyang, Xu Xuetao, Wang Zhenhua, Fang Ping, Mei Tiansheng Chinese Journal of Organic Chemistry 2020, 40 (11): 3738-3747. DOI: 10.6023/cjoc202003022 Published: 28 May 2020 Abstract (206) PDF (910KB)(284) Knowledge map The recent developments in asymmetric organotransition metal-catalyzed electrochemistry (AOMCE) are summarized. AOMCE processes can be divided into oxidative and reductive variants. In terms of oxidations, asymmetric functionalization of olefins, oxidative kinetic resolution of secondary alcohols or aldehydes, and asymmetric C—H functionalization reactions have been developed. Reductive processes discussed include asymmetric electrochemical carboxylation with carbon dioxide, asymmetric electrochemical decarboxylation, and asymmetric reductive coupling reactions. The combination of chiral ligands, transition-metal catalysts, and electrochemistry provides a novel angle by which to address the longstanding fundamental challenge of stereoinduction in traditional electrochemical organic synthesis. Reference | Related Articles | Metrics Reviews Progress in Electrochemical C—H Functionalizations of Aromatic Compounds Wu Yaxing, Xi Yachao, Zhao Ming, Wang Siyi Chin. J. Org. Chem. 2018, 38 (10): 2590-2605. DOI: 10.6023/cjoc201804001 Published: 06 June 2018 Abstract (452) PDF (826KB)(633) Knowledge map Carbon-hydrogen bonds are the most extensive and basic chemical bonds existed in organic compounds. Electrochemical functionalization and direct conversion of aromatic C—H bonds is a green, sustainable, and atomically economical transformation pathway, which avoids the pre-functionalization of reactants. The anodic electrooxidation of aromatics allows the formation of C—X (X=C, N, O, S) bonds and the preparation of fused aromatic rings without the use of oxidants. Certain C—H activation reactions with chemoselectivity and regioselectivity can also be achieved by the optimization of electrode materials, electrolytes, and solvents. Vourious reactions focusing on the electrochemical functionalizations of C—H bonds in aromatic compounds are mainly reviewed. Reference | Related Articles | Metrics Reviews Recent Advances in Organic Electrochemical Synthesis and Application of Hypervalent Iodine Reagents Zhang Huaiyuan, Tang Rongping, Shi Xingli, Xie Lin, Wu Jiawei Chin. J. Org. Chem. 2019, 39 (7): 1837-1845. DOI: 10.6023/cjoc201902006 Published: 09 April 2019 Abstract (353) PDF (714KB)(400) Knowledge map Anodic oxidation of aryl iodine compouds is a green and efficient method for the synthesis of hypervalent iodine reagents. This method replaces chemical reagents with electric current, avoiding the use of expensive and handle difficult oxidants such as m-CPBA, H2O2, oxone, selectfluor etc. Electrochemically generated hypervalent iodine reagents can not only promote fluorination, oxidative cyclization, but also be successfully applied in the total synthesis of natural products. In addition, recyclable aryl iodine mediator can be used to indirect anodic fluorination and easily separated from products. The organic electrochemical synthesis of hypervalent iodine reagents and their applications in various chemical transformations are reviewed. Reference | Related Articles | Metrics Recent Advances on the Photocatalytic and Electrocatalytic Thiocyanation Reactions Zhang Longfei, Niu Cong, Yang Xiaoting, Qin Hongyun, Yang Jianjing, Wen Jiangwei, Wang Hua Chinese Journal of Organic Chemistry 2020, 40 (5): 1117-1128. DOI: 10.6023/cjoc201912011 Published: 21 January 2020 Abstract (440) PDF (820KB)(697) Knowledge map Thiocyanate, as a versatile synthon, which has important application value in many fields such as pharmaceutical, pesticide and materials. The photocatalytic and electrocatalytic thiocyanation reactions have been widely concerned in organic chemistry due to the advantages of green, efficiency and safety. In this review, the cross-coupling/thiocyanation reactions based on the photocatalytic and electrocatalytic are described, which is expected to be helpful in exploring the green synthesis of thiocyanates compounds. Reference | Related Articles | Metrics