Article
Chemistry, Organic
Shuling Yu, Chao Hong, Zhanxiang Liu, Yuhong Zhang
Summary: In this study, the efficient synthesis of pyranones was achieved through a three-component cascade reaction under ruthenium catalysis using readily available acrylic acids, ethyl glyoxylate, and p-toluenesulfonamide. For the first time, the nucleophilic addition of the vinylic C-H bond of acrylic acids across aldehyde was achieved, followed by intramolecular cyclization and subsequent second insertion to aldehyde to form substituted butenolides. The sulfonamides were eliminated at higher temperature to yield the pyranones.
Article
Chemistry, Multidisciplinary
Qiang Ma, Ming Li, Zhuo Chen, Shao-Fei Ni, James S. Wright, Li-Rong Wen, Lin-Bao Zhang
Summary: An electrochemical protocol was developed for the synthesis of 2,3-disubstituted quinolines. The method is simple, mild, and does not require noble catalysts or external oxidants. It shows excellent regioselectivity and can tolerate various functional groups. The scaled-up experiment and follow-up procedures demonstrated the practicality of electrochemical synthesis.
Review
Chemistry, Multidisciplinary
Pallavi Singh, Kishor Kumar Chouhan, Arup Mukherjee
Summary: Ruthenium-catalyzed C-H activation is widely used in organic synthesis and molecular science, with a focus on the intramolecular functionalization which offers atom economy and easy purification of products. The development of new synthetic strategies in organic chemistry has gained significant interest in recent years.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Physical
Xue-Ya Gou, Yuke Li, Yu-Yong Luan, Wei-Yu Shi, Cui-Tian Wang, Yang An, Bo-Sheng Zhang, Yong-Min Liang
Summary: This study reports the combination of free radical cyclization and ruthenium-catalyzed meta-selective C-H functionalization for the synthesis of arylpyrrolidone derivatives, demonstrating high meta-site selectivity and wide applicability.
Article
Chemistry, Applied
Zuguang Yang, Pinyi Li, Zhengkai Chen, Xiao-Feng Wu
Summary: A rhodium(III)-catalyzed C-H activation/[4+1] annulation reaction has been developed for the synthesis of diverse trifluoroacetimidoyl-substituted 11H-isoindolo[2,1-a]indoles. The reaction cascade involves C-H imidoylmethylation, tautomerization, and AgOAc-mediated C-N bond formation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Shao-Yong Chen, Yi-Chuan Zheng, Xu-Ge Liu, Jia-Lin Song, Lin Xiao, Shang-Shi Zhang
Summary: The indole-substituted trifluoromethyl sulfonium ylide was synthesized via the Cp*Rh(III)-catalyzed addition of diazocarbenoid to trifluoromethylthioether, and it represents the first example of an Rh(III)-catalyzed diazo-carbenoid addition reaction with trifluoromethylthioether. Several types of indole-substituted trifluoromethyl sulfonium ylide were prepared using mild reaction conditions. The method demonstrated high compatibility with functional groups and a wide substrate scope. Furthermore, it was found to be complementary to the method previously disclosed using a Rh(II) catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhuo Wu, Feng Wei, Bin Wan, Yanghui Zhang
Summary: The report discusses a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. This reaction allows for the dimethylation of iodoarenes at the ipso- and meta-positions, and subsequent C-H activation to form new C-C bonds, leading to the synthesis of important organic compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Jayanta Ghorai, Kuppan Ramachandran, Pazhamalai Anbarasan
Summary: A rhodium-catalyzed redox-neutral annulation method has been successfully developed for the synthesis of substituted indole derivatives from N-acetoxyacetanilides and alkynes. The method shows excellent efficiency and wide functional group tolerance, allowing for the synthesis of a variety of 2,3-diarylindoles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Xue-Yi He, Zhong-Xia Wang
Summary: The ruthenium(II)-catalyzed reaction between aniline derivatives and allylamines was used to synthesize 2-methylindoles via C-H/C-N bond activation. The most effective directing group is the 4,5-dimethyl pyrimidin-2-yl group attached on the nitrogen atom of anilines, while N-allyl-4-fluoro-N-methylaniline is the optimal allylamine. The cyclization products were obtained in yields ranging from 16% to 96%. The reaction does not require an external oxidant, and a possible mechanism is proposed.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yong Zhang, Ya-Kui Sun, Ya-Ping Chang, Hui Shao, Yu-Ming Zhao
Summary: The rapid construction of molecules with all-substituted quaternary stereocenters is a significant but challenging task in organic synthesis. This study reports a novel palladium-catalyzed cascade reaction between alkene-tethered aryl iodides and carbon monoxide, providing a practical and powerful method for synthesizing complex polycyclic molecules containing aryl-substituted quaternary stereocenters. Mechanistic studies suggest that the reaction proceeds through a Heck-type carbonylative cyclization followed by a ketene-involved Friedel-Crafts acylation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Mengyang Shen, Jie Zhao, Yuanshuang Xu, Xinying Zhang, Xuesen Fan
Summary: This novel synthesis method of dihydroquinolinone derivatives involves an unprecedented cascade reaction, which includes the in-situ formation of aryne and its addition with pyrazolidinone, followed by N-N bond cleavage and intramolecular C-C bond formation. Compared to existing methods, this protocol offers advantages such as multiple transformations in one pot, a broad substrate scope, mild reaction conditions, and good tolerance of various functional groups. Additionally, the products obtained from this method demonstrated significant in vitro antiproliferative activity in selected human cancer cell lines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qiongwen Kang, Mengdan Wang, Zongkang Wang, Lu Cheng, Yilin Zhu, Chengyu Wang, Yanzhong Li
Summary: A base-promoted selective C2-N1 ring-expansion reaction of indolones toward substituted quinolines under mild conditions has been developed, achieving the cleavage of one C-N bond and three C-C bonds, and the formation of one C-N and three C-C bonds in one step. This is the first example of a transition-metal free ring-expansion reaction of indolones via the selective insertion of alkynoates into the C2-N1 bond.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Chuan-Chong Peng, Fang Long, Yun-Chu Hu, Zheng-Rui Zhou, Kai-Yi Zhang, Ru Wang, Meng-Hua Ye, Hong-Bo Xiao, Li-Jun Wu
Summary: A novel and mild metal-free catalyzed radical-mediated cascade spirocyclization of N-benzylacrylamides with polyhaloalkanes has been proposed, enabling the preparation of polyhalo-substituted azaspirocyclohexadienones. This protocol allows for the easy construction of multiple chemical bonds and a spiro ring in a single reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Editorial Material
Chemistry, Multidisciplinary
Terence Wu, Michael F. Greaney
Summary: Diaryliodonium salts are versatile arylating agents, but they generally have poor atom economy. In this article, Olofsson and his colleagues describe a novel chemoselective SNAr reaction that incorporates the iodoarene component in a cascade arylation, achieving excellent atom economy.
Article
Chemistry, Multidisciplinary
Marie Peng, Denis Ari, Thierry Roisnel, Henri Doucet, Jean-Francois Soule
Summary: We present a versatile Rh(i)-catalyzed cascade reaction that combines C(sp(2))-H bond functionalization and amidation between N-arylphosphanamines and acrylates. This innovative approach allows for the rapid synthesis of dihydroquinolinone scaffolds, which are commonly found in various pharmaceuticals. The involvement of a Rh-H intermediate and the substrate inhibition through catalyst saturation were revealed through detailed mechanistic investigations.
