Article
Chemistry, Organic
Hui-Xin Xiao, Pan-Pan Li, Bin Pan, Wu Liang, Fei Du, Yu Yu
Summary: A new alkoxycarbonylation/cyclization reaction of unactivated alkenes containing heterocycles is reported. Silver carbonate is employed as the catalyst under photoirradiation. The method provides efficient access to valuable pharmaceutical compounds and natural product analogues containing quinazolinone-fused esters.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mohana Reddy Mutra, T. L. Chandana, Yun-Jou Wang, Jeh-Jeng Wang
Summary: Environmentally friendly acid-catalyzed ynamide N-Csp bond cleavage, alkyne migration, and stereospecific functionalization with anisole derivatives for the synthesis of challenging cis-alkene tethered indole scaffolds in a very short reaction time (5-10 min).
Article
Chemistry, Applied
Kang Guo, Chen Gu, Yun Li, Xiaofei Xie, Honglin Zhang, Kang Chen, Yingguang Zhu
Summary: In this study, a photoredox catalyzed trifluoromethyl radical-triggered trifunctionalization of 5-hexenenitriles via cyano group migration is reported. The migration of the cyano group shows high chemo-selectivity even in the presence of aryl or heteroaryl groups as competitors. This protocol provides a simple access to CF3-containing compounds with high molecular complexity and functional group diversity. The successful gram-scale reaction and the versatility of the products in derivative synthesis illustrate the potential value of this transformation in synthetic chemistry.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Xiao Qian, Tong Qing-Xiao, Zhong Jian-Ji
Summary: Benzazepines, important nitrogen-containing heterocyclic compounds, are widely found in natural products and pharmaceuticals and possess versatile biological activity. The green and efficient synthesis of benzazepines has attracted great attention. Radical cascade cyclization reactions have emerged as a powerful tool for constructing benzazepines due to their unique advantages. This minireview systematically summarizes the research progress on the synthesis of benzazepines via radical cascade cyclization reactions in the past five years, including photochemical, electrochemical, and thermochemical reactions.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sun Xin, Qu Chaofan, Ma Chaorui, Zhao Xiaowei, Chai Guobi, Jiang Zhiyong
Summary: The biological importance of quinoxalin-2(1H)-ones has driven the development of efficient synthetic methods. In recent years, C3-H functionalization has become a popular strategy, especially using photocatalysis to generate radical intermediates. This study reports a cascade reaction strategy involving radical addition to quinoxalin-2(1H)-ones and subsequent reactions to generate a series of valuable quinoxalin-2(1H)-one derivatives. The reaction partners used in this study are 2-bromo-1-arylethan-1-ones.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jia-Yin Wang, Sai Zhang, Yao Tang, Shenghu Yan, Guigen Li
Summary: The Cu(I)-catalyzed annulation-halotrifluoromethylation and cyanotrifluoromethylation of enynones have been successfully developed, allowing for the construction of quaternary carbon-centered 1-indanones through multibond formations with moderate to good chemical yields. The reaction of enynones with Togni's reagent and chloro- or bromotrimethylsilane yielded halo- and CF3-containing 1-indenones, while the addition of K3PO4 as a base resulted in the formation of cyano-anchored (Z)-1-indanones as the major stereoisomeric products. This strategy exhibits excellent compatibility with a wide range of enynones.
Article
Chemistry, Organic
Yuki Yoshida, Haruka Takeuchi, Kohei Nakagawa, Toshiki Fujii, Norihito Arichi, Shinya Oishi, Hiroaki Ohno, Shinsuke Inuki
Summary: In this study, it was found that simple biphenyl substrates derived from amino acids can participate in a radical cascade reaction under visible light irradiation in the presence of [Ir{dF(CF3)ppy}(2)(dtbpy)]PF6, enabling the direct construction of bicyclo[2.2.2]octene structures. Isotopic labeling experiments suggested that intramolecular hydrogen atom transfer is involved in the cascade processes.
Article
Chemistry, Applied
Elisa Brambilla, Silvia Meraviglia, Edoardo Moneta, Donatella Nava, Silvia Rizzato, Giorgio Abbiati, Valentina Pirovano
Summary: A photoredox-promoted approach for the synthesis of [1,4]diazepino[1,7-a]indol-6(7H)-ones starting from N-indolyl phenylacrylamides and aroyl chlorides as radical source is reported. This method involves a cascade radical addition on C-C double bond followed by intramolecular cyclization at indole C2-position, resulting in the formation of two diastereomeric indole-fused 1,4-diazepinones characterized by a N-C(aryl) axial chirality, with yields ranging from 51% to 99%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Shengxian Zhai, Shuxian Qiu, Shuai Yang, Bingyan Hua, Yongsheng Niu, Chuchu Han, Youzhu Yu, Yuchao Li, Hongbin Zhai
Summary: A metal-free radical cascade reaction was developed for the synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolin-6(5H)-one derivatives using readily available sulfonyl hydrazides and N-substituted 2-aryl indoles. The reaction employed a TBAI-TBHP catalytic system and yielded a broad series of structurally diverse derivatives in moderate to excellent yields. The reaction exhibited mild reaction conditions, operational ease, scalability, and high tolerance towards functional groups.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Till Drennhaus, Dirk Leifert, Jessika Lammert, Jan Philipp Drennhaus, Klaus Bergander, Constantin G. Daniliuc, Armido Studer
Summary: Enantioenriched chiral indoles were synthesized through a mild and efficient radical cascade reaction. The targeted indoles were accessed by stereochemical control using a chiral copper-bisoxazoline complex. The method demonstrated excellent enantioselectivity and good yields, and the mechanism was elucidated through mechanistic studies.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Feng Chen, Xiu-Hua Xu, Lingling Chu, Feng-Ling Qing
Summary: A photochemically induced, nickel-catalyzed radical cross-coupling reaction has been developed for the synthesis of alpha-aryl-alpha-trifluoromethyl alcohols. This reaction utilizes a photoinduced charge transfer process between Hantzsch ester and phthalimido trifluoroethanol to generate a radical intermediate for the cross-coupling with aryl bromides. The protocol is mild and operationally simple, without the need for exogenous photocatalysts or stoichiometric metal reductants, and exhibits broad substrate compatibility and excellent functional group tolerance.
Article
Chemistry, Multidisciplinary
Fengqian Zhao, Xing-Wei Gu, Robert Franke, Xiao-Feng Wu
Summary: In this study, a new procedure for the 1,2-dicarbonylative cyclization of 4-aryl-1-butenes with alkyl bromides was developed. A simple copper catalyst was used to introduce two molecules of carbon monoxide into the double bond, resulting in the formation of four new C-C bonds and a new ring. The reaction produced various alpha-tetralones and 2,3-dihydroquinolin-4-ones in moderate to good yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Li Liu, Yage Zhang, Wenyan Zhao, Jinxia Wen, Chunping Dong, Caijuan Hu, Jian Li
Summary: A method for photocatalyzed cascade double C-C formation via sp2 C-H bond activation of diarylamines with hypervalent iodine diazo reagents was developed. The method tolerated a variety of diarylamines and hypervalent iodine(III) reagents and efficiently provided a range of substituted acridines with yields ranging from moderate to excellent. The protocol introduced diazo groups onto diarylamines and enabled subsequent late-stage assembly point functionalization with the diazonium structure, forming two new C-C bonds in a sequential fashion.
Article
Multidisciplinary Sciences
Junli Chao, Yuanyuan Yue, Ke Wang, Xiaohui Guo, Chunying Sun, Yue Xu, Jianming Liu
Summary: A concise copper-catalyzed oxidative dehydrogenative dearomatization method was developed for the direct synthesis of spirocyclic indolenines containing fluorene and indeno[2,1-b]indole groups. The utility of this method was demonstrated by achieving dual oxidative dehydrogenative dearomatization and producing the desired spirocyclic indolenines with fluorene groups. Mechanistic analyses revealed that the C-H cleavage of the phenyl ring was not involved in the rate-limiting step.
Article
Chemistry, Organic
Hua Zhang, Bei Wang, Hong Xu, Fu-Yu Li, Ji-Yu Wang
Summary: A convenient method for the synthesis of naphthodihydrofurans has been developed using iron(iii)-catalyzed cascade reaction of reducing radicals. This protocol allows for the easy preparation of a variety of spiro and polycyclic naphthodihydrofurans, which can be further converted to polycyclic ethers and 2,3-dihydronaphtho[1,2-b]furan-4,5-diones by derivatizing naphthodihydrofurans.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Weijie Yu, Shuwu Yang, Fei Xiong, Tianxiang Fan, Yan Feng, Yuanyuan Huang, Junkai Fu, Tao Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Haiyan Li, Long Chen, Tao Wang, Fei Xiong
Summary: A new synthetic method of coumarins 3-aldehyde via visible light stimulation and oxidation promotion cascade radical cyclization/hydrolysis process is reported, with good to excellent yields and valuable synthetic applications.
Article
Chemistry, Multidisciplinary
Yue Wu, Peng Guo, Long Chen, Weijie Duan, Zengzhuan Yang, Tao Wang, Ting Chen, Fei Xiong
Summary: The research achieved direct formylation of benzothiazo/les and isoquinolines through a novel iron-catalyzed Minisci-type oxidative coupling process, with exceedingly mild reaction conditions and broad functional group tolerance.
CHEMICAL COMMUNICATIONS
(2021)
