Article
Chemistry, Organic
Shangyuan Wang, Jiangjie Zhang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed cascade radical cyclization and carbonylation reaction of 1,7-enynes with perfluoroalkyl iodides and alcohols has been developed. The use of benzene-1,3,5-triyl triformate (TFBen) as the CO source enables the construction of 3,4-dihydroquinolin-2(1H)-one skeletons with the incorporation of both perfluoroalkyl and carbonyl units. This method provides a facile and efficient approach for the synthesis of various 3,4-dihydroquinolin-2(1H)-one derivatives with moderate to high yields and excellent E/Z selectivity.
Article
Chemistry, Organic
Chunxiang Pan, Gaowei Wang, Hengyuan Zhao, Jianxiao Ni, Ruifeng Fan, Yongyun Zhou, Yuanbin Zhu, Shiyuan Wu, Baomin Fan
Summary: An efficient stereoselective cobalt-catalyzed hydrovinylative cyclization of 1,6-enynes with chalcones to obtain functionalized pyrrolidines has been developed. The products were furnished in good yields with up to 93% ee. A plausible mechanism through which the transformation was initiated by cyclization of 1,6-enynes is proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Biochemistry & Molecular Biology
Mengting Liu, Xiongda Xie, Ming Bao, Zhijing Zhang, Wenhao Hu, Yu Qian, Xinfang Xu
Summary: A gold-catalyzed carbocyclization/imidization cascade reaction has been developed for the synthesis of functionalized nitrones. The resulting products can be further converted into substituted naphthalenol analogues and exhibit potential tumor suppression activity.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Organic
Pengbo Zhang, Guo Yu, Ning Zhao, Shanshan Zhang, Minghui Zhang, Longyu Wang, Zhaoting Li, Jianxi Ying, Xia Gao
Summary: The Pd-catalyzed difluoroalkylation/cyclization/phosphinoylation reaction successfully allows the formation of C-sp3-C-F2, C-sp3-C-sp2, and C-sp2-P(O) bonds in one step, providing a straightforward route to difluoroalkyl-containing tetrasubstituted alkenylphosphine oxides with complete stereoselectivities under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jhen-Kuei Yu, Constantin Czekelius
Summary: An efficient protocol for the synthesis of 3-ethynyl-2-aryl-bicyclo[3.1.0]hexenes through gold-catalyzed enyne cyclization was established. Depending on the substitution pattern, unusual cationic rearrangements of the corresponding gold carbene were revealed, leading to the formation of cyclohexadienes or 5,9-methanobenzo[8]annulene derivatives, respectively.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Perla Bharath Kumar, Chittala Emmaniel Raju, Patel Hinal Chandubhai, Balasubramanian Sridhar, Galla V. Karunakar
Summary: Molecules obtained from nature have various biological applications in medicinal chemistry, agrochemicals, and material sciences. Oxygen-containing molecules such as chromenes and benzochromenes are found to have potential biological applications.
Article
Chemistry, Multidisciplinary
Shivam A. A. Meena, Poonam Sharma, Akhilesh K. K. Verma
Summary: A transition-metal-free one-pot synthesis of di-functionalized succinimides has been developed, which involves a radical cascade seleno/thiosulfonation of aza-1,6-enynes in an atom economical manner. This method allows the synthesis of highly decorated succinimides with excellent stereoselectivity under mild reaction conditions. The proposed radical pathway is well supported by control experiments. The reaction demonstrates advantageous features including operational simplicity, atom economy, and broad substrate scope.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Muniganti Naveen Kumar, Vavilapalli Suresh, Attunuri Nagireddy, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
Summary: Annulations of unsaturated systems through C-H activation are a powerful tool for producing multicyclic scaffolds. Employing a dual coordination strategy with coordinating centers in both annulation partners can lead to remarkable selectivities. In this study, we report a Pd-catalyzed regioselective rollover cascade dual C-H annulation for constructing phenanthrene scaffolds. Mechanism studies, including control experiments, KIE, and deuteration experiments, were conducted, and downstream transformations and scaled-up reactions were performed to evaluate the robustness of the transformation.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Anjia Liu, Hongbo Qi, Dongmei Chi, Shufeng Chen
Summary: This study describes an efficient Pd-catalyzed cascade alkynylation of arylphenol-tethered alkynes with alkynyl bromides. This method can generate various conjugated 1,3-enynes with a polysubstituted spirocyclohexadienone and an all-carbon tetrasubstituted alkene moiety. The resulting products can also undergo ring-expansion and cyclization transformations under different conditions, leading to diverse fused cyclic scaffolds.
Article
Biochemistry & Molecular Biology
Itaru Nakamura, Mai Tachibana, Riku Konta, Hiroki Tashiro, Masahiro Terada
Summary: Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of IPrCuBr and AgSbF6 afford meta-aminophenol derivatives through a [1,3]-rearrangement and an oxa-Michael reaction.
Article
Chemistry, Organic
Zhi-Kai Liu, Ying Yang, Zhuang-Ping Zhan
Summary: A general and efficient palladium-catalyzed hydroalkynylation method has been developed for the synthesis of (E)-1,3-enyne derivatives with high regio- and stereoselectivity. This method is compatible with a broad range of substrates and expands the synthetic potential of these scaffolds in organic synthesis and medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xiai Luo, Wenguang Li, Haiyan Lu, Guobo Deng, Yuan Yang, Chunming Yang, Yun Liang
Summary: This study achieved simultaneous C2-H arylation and C8-H alkylation of the naphthalene ring, providing an efficient method for synthesizing aryl-substituted spirocyclic oxindoles. The protocol enables three C-C bonds formation via intramolecular Heck reaction.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Jingwen Wei, Yangyang Xing, Xiaohan Ye, Bao Nguyen, Lukasz Wojtas, Xin Hong, Xiaodong Shi
Summary: In this study, a new synthetic strategy for enantioselective 1,2-dihydropyridine synthesis was reported. Using the gold-catalyzed intermolecular condensation of amine and diyne-ene, the synthesis was achieved through a formal [3+2+1] fashion with up to 95% yield and up to 99% enantiomeric excess (e.e.).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Quan Huang, Mingming Zhao, Yiqiang Yang, Yan-Ning Niu, Xiao-Feng Xia
Summary: This paper describes a mild and efficient intramolecular oxidative cyclization reaction using substituted aromatic enamines and the C(sp(3))-H bond adjacent to nitrogen with alkynes or alkenes to produce multi-substituted quinolines and indoles, utilizing dioxygen as an oxidant. Visible light irradiation in combination with a simple and inexpensive copper catalyst enables functionalization of internal alkynes or alkenes via an intramolecular radical cyclization strategy without the need for additional photosensitizers. Preliminary mechanistic studies, including radical capture reactions, isotope labeling experiments, and fluorescence quenching study, have also been conducted.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Xin-Ming Xu, Sen Chen, Wenzhong Li, Xuesi Zhang, Zhongyuan Zhao, Xinyue Cao, Yuhang Yao, Xiangmin Wang, Zu-Li Wang
Summary: A gold(I)-catalyzed intramolecular cascade reaction of tertiary enamides has been developed for the preparation of diverse pyrido[2,1-a]isoquinoline derivatives with good functional group tolerance. The reaction mechanism involves a nucleophilic addition of the enamide to an alkynyl group, followed by the capture of the acyliminium ion by an electron-rich aromatic component. Scale-up experiments and further transformations of pyrido[2,1-a]isoquinolines demonstrate the utility of this methodology.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
