Article
Chemistry, Organic
Changlei Zhu, Max Nurko, Cynthia S. Day, John C. Lukesh
Summary: This study describes an efficient and novel approach to synthesizing 3-selenylquinolines. By utilizing a combination of CuCl2 and air as catalyst, key Se-C and C-C bonds were formed in a single step. The method showcased moderate to excellent yields under mild conditions, highlighting its versatility and usefulness.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ashis Mathuri, Buddhadeb Pal, Milan Pramanik, Prasenjit Mal
Summary: Here we describe a cascaded chalcogenation reaction for the synthesis of selectively either 3-sulfenylated/selenylated coumarins or spiro[4,5]trienones using a visible light photocatalyst. The reaction is initiated by radicals and the presence of -OMe or -F substituent at the para position stabilizes the allylic radical intermediate, promoting spiro-cyclization. Otherwise, 6-endo-trig cyclization leads to the formation of 3-sulfenylated/selenylated coumarins. The formation of new C-S/C-Se, C-C, and C=O bonds occurs in a single step. Quenching studies, EPR experiments, light ON-OFF experiments, and radical trapping experiments provide insights into the radical-based mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zheng Liu, Youkun Wang, Jianfeng Huo, Xiao-Jun Li, Shengnan Li, Xiaoning Song
Summary: A new synthetic method was developed for the synthesis of fully substituted isothiazolones using water-mediated reaction conditions, which showed good functional group tolerance, mild reaction conditions, and operational simplicity, providing a potential pathway for applications in pharmaceutical chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Ya-Nan Li, Fan Chen, Xing-Guo Zhang, Hai-Yong Tu
Summary: An iodine-mediated radical cyclization reaction of o-vinylaryl isocyanides with disulfides or diselenides has been developed, providing an atom-economic method for the regioselective construction of 2-chalcogenated quinolines with high yields by incorporating both chalcogen atoms of the disulfides or diselenides.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yang-Tong Ma, Chao Lin, Xiao-Bo Huang, Miao-Chang Liu, Yun-Bing Zhou, Hua-Yue Wu
Summary: This study presents the (NH4)(2)S2O8-promoted cross-coupling reaction of thiols/diselenides and sulfoxides to form unsymmetrical disulfides/selenosulfides. Control experiments demonstrate that (NH4)(2)S2O8 acts as both an acid and an oxidant, and the reaction involves both ionic and radical routes. Kinetic isotope effect experiments reveal that the C-H bond cleavage of sulfoxides is involved in the rate-limiting step.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Organic
Jieru Hui, Yanlong Ma, Jiaji Zhao, Hua Cao
Summary: This review systematically examines the current and latest synthetic strategies using radical species or radical intermediates for synthesizing indolizines and their derivatives. The review is classified into two parts based on the type of building blocks used for indolizine ring construction and the type of radical trigger for indolizine derivative construction. We anticipate that this review will provide a deep understanding of this topic and help researchers develop novel approaches for the synthesis of indolizine and its derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Pengpeng Tan, Liwang Lu, Shilong Wang, Junxin Wang, Jiayang Chen, Yijia Zhang, Lei Xie, Shubin Yang, Jinchun Chen, Zhen Zhang
Summary: A cascadeselenylation/cyclization of dienes with diselenides has been achieved under visible-light irradiation or electrolysis conditions. Employing O-2 or electricity as a green oxidant, this method offers a green and efficient approach for the synthesis of various biologically important seleno-benz-[b]-azepine derivatives in moderate to good yields. The use of direct sunlight irradiation and gram-scale reactions make this approach practical and attractive.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chenyang Wang, Peng Shi, Carsten Bolm
Summary: In this study, dichloro- and dibromomethane were utilized as halogen sources to convert NH-sulfoximines to N-halo derivatives, using an in situ formed sulfoximidoyl-containing hypervalent iodine reagent under visible light. The reactions were carried out in air without the need for catalysts or additives, and the products were obtained in good to excellent yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Pijush Kanti Roy, Sayuri Okunaka, Hiromasa Tokudome, Yutaka Hitomi
Summary: In this study, it was found that thioanisole derivatives can undergo dual carbon-carbon bond-forming reactions with maleimide derivatives in the presence of titanium dioxide under blue light irradiation. This reaction leads to the synthesis of thiochromenopyrroledione derivatives and succinimide derivatives. The reaction yield and selectivity can be influenced by the substituents on the starting materials, suggesting a charge transfer mechanism involving one-electron oxidation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Tong-Yang Cao, Lin Qi, Li-Jing Wang
Summary: We describe a facile switchable regioselective 7-endo or 6-exo iodocyclization of O-homoallyl benzimidates, which provides a controllable synthesis of various iodo-substituted 1,3-oxazines and tetrahydro-1,3-oxazepines. These products can undergo further substitution reactions to yield a series of functionalized heterocyclic compounds. The developed protocol offers mild conditions, simplicity in operation, and excellent compatibility with functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhen Zhang, Pengpeng Tan, Shilong Wang, Huichao Wang, Lei Xie, Yue Chen, Liangliang Han, Shubin Yang, Kai Sun
Summary: A novel visible-light-promoted selective sulfonylation and selenylation of dienes with selenosulfonates has been developed, providing mild access to a wide range of sulfonyl benzo-[b]-azepinones and seleno-benzo-[b]-azepines. Preliminary mechanistic studies suggest that the sulfonylation involves a sulfonyl radical engaged cascade process, and the selenylation is accomplished through a sequential oxidation/electrophilic cyclization process. The large-scale operation and late-stage modification experiment reveal the promising utility of this protocol.
Article
Chemistry, Multidisciplinary
Jin-Wei Yuan, Qian Chen, Wen-Tao Wu, Jian-Jun Zhao, Liang-Ru Yang, Yong-Mei Xiao, Pu Mao, Ling-Bo Qu
Summary: A cascade annulation reaction of terminal alkynyl amides with diselenides has been successfully carried out to construct 3-arylselenenyl spiro[4.5]trienones under mild conditions using Selectfluor as the sole oxidant. Additionally, 3,4-bisarylselenenyl spiro[4.5]trienones were synthesized via a cascade annulation reaction using transition-metal copper as a catalyst. This spirocyclization process involves sequential C(sp)-Se and C(sp)-C(sp(2)) bond formation, accompanied by the introduction of a carbonyl oxygen.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Biwei Zhang, Hongjian Yang, Taimin Wang, Xuanzhen Han, Haiyan Sun, Lijing Fang, Hongbin Zhai, Bin Cheng
Summary: The microwave-promoted multicomponent reaction successfully synthesized SH-chromeno[2,3-d]pyrimidin-5-one derivatives in good to excellent yields under catalyst-free and solvent-free conditions. This unexpected annulation pathway further expanded the synthetic application of paraformaldehyde as a C1 building block.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yao-Bin Shen, Jian-Qiang Zhao, Zhen-Zhen Ge, Zhen-Hua Wang, Yong You, Ming-Qiang Zhou, Wei-Cheng Yuan
Summary: A HFIP-promoted transition metal-free intramolecular dearomative annulation reaction has been developed for the synthesis of structurally diverse substituted 3,4-dihydroquinolizin-2-ones under mild conditions, affording moderate to good yields of the desired products.
Article
Chemistry, Multidisciplinary
Biplab Mondal, Chenna Jagadeesh, Dinabandhu Das, Jaideep Saha
Summary: We demonstrated that gamma-aminocyclopentenones can serve as suitable substitutes for reactive cyclopentadienone via a pseudocine-substitution manifold. This approach allows for orchestrated annulation with specific bis-nucleophiles, leading to the synthesis of complex beta,gamma-annulated cyclopentanoids or indole-based polycyclic architectures. It represents a generalized method for the direct, regioselective, and stereoselective beta,gamma-functionalization of monosubstituted or unsubstituted aminocyclopentenones.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Jia-Hao Chen, Wasim Ahmed, Ming-Hua Li, Zhao-Dong Li, Zi-Ning Cui, Ri-Yuan Tang
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Zhu Zhu, Jinggong Liu, Shoucheng Dong, Bolai Chen, Zhenghui Wang, Ri-yuan Tang, Zhaodong Li
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Yong-Chao Gao, Zi-Hao Huang, Zhao-Sheng Zhang, Jin-Xin Xie, Zi-Ning Cui, Ri-Yuan Tang
SYNTHESIS-STUTTGART
(2020)
Article
Chemistry, Organic
Zhuoxian Shao, Shaoyi Zhang, Yihan Chen, Yun-Lin Liu, Ri-Yuan Tang, Zhaodong Li
Article
Chemistry, Organic
Zhuo-Bin Huang, Xue-Ying Guo, Zi-Hao Huang, Ming-Hua Li, Shou-Cheng Dong, Ri-Yuan Tang
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Jian-Xiong He, Huan-Yu Pan, Li Xu, Ri-Yuan Tang
Summary: Aflatoxins are highly toxic carcinogens, and molecular imprinting polymers have been widely applied for their detection and separation. Different polymerization methods and applications of molecular imprinting polymers in aflatoxin detection were reviewed in this study.
JOURNAL OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Wasim Ahmed, Zi-Hao Huang, Zi-Ning Cui, Ri-Yuan Tang
Summary: This study reports the synthesis of unique mesoionic thiazoloisoquinolinium thiolates via cycloaddition reaction, which shows good bioactivity against the chlorophyll of duckweed.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Yiming Du, Shuxin Chen, Ao Huang, Yihan Chen, Yun-Lin Liu, Gaopeng Song, Ri-Yuan Tang, Hanhong Xu, Guangkai Yao, Zhaodong Li
Summary: This article reports a versatile and expeditious method for site-selective C-H fluoromethylation of aryl iodides via Pd/norbornene cooperative catalysis. It can serve as a robust toolbox for the diversity-oriented synthesis (DOS) of fluoromethylated arenes. The method features the use of low-cost industrial raw material CH2IF as the fluoromethyl source, excellent functional group tolerance, and broad ipso termination scope. It can also be applied to the late-stage modification of biorelevant molecules.
Article
Chemistry, Multidisciplinary
Shuxin Chen, Xue Liu, Kaidian Li, Wenchao Yang, Jian Lin, Ri-Yuan Tang, Hanhong Xu, Zhaodong Li
Summary: A novel approach based on Pd/norbornene cooperative catalysis is presented for the efficient assembly of beta-fluoroalkylated arenes. The method shows excellent functional group tolerance and a wide range of ipso termination reactions. Additionally, it enables the synthesis of diverse fluorinated macrolactones under mild reaction conditions, which is otherwise extremely challenging.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Medicinal
Jinxin Xie, Lijuan Wang, Xiaoyong Zhang, Yiyang Li, Xin Liao, Caixin Yang, Ri-Yuan Tang
Summary: Aryloxyethyl propiolates and their homologues are promising anti-MRSA agents with multiple targets, as they can destroy the cell wall and cell membrane, inhibit the formation of a biofilm, and bind to the DNA of MRSA.
ACS INFECTIOUS DISEASES
(2022)
Article
Chemistry, Applied
Guangkai Yao, Chuanle Zhu, Tianyi Qin, Mengfan Wang, Zhixiu Sun, Ri-Yuan Tang, Chen Zhao, Huanfeng Jiang, Hanhong Xu
Summary: The oxidative [3+2+1] annulation reaction of aldehydes, 5-aminopyrazoles, and nitriles under the oxidation of I-2/O-2 produces valuable pyrazolo[3,4-d]pyrimidines in yields of 27%-91%. This reaction is notable for being transition-metal free, operationally simple, having a broad substrate scope, good functional group tolerance, and being scalable.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Agriculture, Multidisciplinary
Zi-Hao Huang, Xue-Ying Guo, Lan-Tu Xiong, Li Dong, Jin-Tong Jian, Lin-Hao Wei, Ri-Yuan Tang, Han-Hong Xu
Summary: In this study, novel N-difluoromethyl triazole selenoureas have been developed as a versatile artificial organoselenides defense (AOSeD) for controlling pests, phytopathogenic fungi, and weeds. Furthermore, the AOSeD is safe for tomato plants and Brassica campestris.
ACS AGRICULTURAL SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Jinxin Xie, Benjian Liao, Hui Zhu, Yongfei Yu, Ri-Yuan Tang
Summary: The study synthesized novel 2-methyl-3-furyl sulfide flavor derivatives and evaluated their antimicrobial activity against foodborne bacteria and fungi. Fifteen compounds were found to have potential as preservatives for food production, with some showing better antimicrobial activity than traditional control groups.
Review
Agriculture, Multidisciplinary
Jinxin Xie, Benjian Liao, Ri-Yuan Tang
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2020)
Article
Chemistry, Organic
Zhuo-Bin Huang, Xiong-Jian Xia, Zi-Hao Huang, Li Xu, Xiao-Yong Zhang, Ri-Yuan Tang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
