Article
Chemistry, Organic
Min Zhang, Zhangyi Fu, Anping Luo, Xingwen Pu, Menglei Wang, Ying Huang, Yudong Yang, Jingsong You
Summary: The study presents a concise route for site-selective arylation of polycyclic aromatic hydrocarbons with easily available aryl sources, contributing to the bottom-up preparation of pi-extended PAHs. Additionally, a C8-H annulation protocol has been developed to rapidly assemble benzanthrones by simply switching the solvent to 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP).
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Shuaishuai Song, Yunfei Lai, Zekun Tuo, Jianming Zhong, Wang Zhou
Summary: A rhodium(III)-catalyzed oxidative cyclization of chalcones with internal alkynes is reported, resulting in the formation of biologically important 3,3-disubstituted 1-indanones and reusable aromatic aldehydes. This transformation exhibits a unique (4+1) reaction mode, excellent regioselectivity, broad substrate scope, ability to construct quaternary carbon centers, and scalability. Steric hindrance from the substrate and ligand likely controls the chemoselectivity of this carbocyclization. Importantly, this discovery enables a practical two-step protocol to switch the overall reaction from a (3+2) to a (4+1) annulation of acetophenones with internal alkynes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Qiuyu Li, Jiajia Li, Jie Zhang, Shu Wu, Yu Zhang, Aijun Lin, Hequan Yao
Summary: A palladium-catalyzed asymmetric intramolecular alkene-alkyne coupling reaction has been developed for the synthesis of enantionenriched bicyclo[3.2.1]octadienes. The products exhibit an unusual iodination-induced 1,2-acyl migration, leading to the formation of iodinated bicyclo[3.2.1]octadienes with three vicinal stereocenters. The enone and isolated olefin motifs in the products provide versatile handles for further elaboration.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
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)
Review
Chemistry, Physical
Ruimao Hua
Summary: Isoquinolones, important nitrogen-heterocyclic compounds with versatile biological and physiological activities, have seen significant advances in synthetic methods in recent years. This review highlights the construction of isoquinolone rings with atom- and step-economy, focusing on intermolecular annulation protocols, intramolecular cyclization, and synthesis of isoquinolone-fused rings.
Article
Chemistry, Physical
Yeong Bum Kim, Dongwook Kim, Shashikant U. Dighe, Sukbok Chang, Jung-Woo Park
Summary: This research describes a novel cobalt-catalyzed reaction for the synthesis of terminal branched allylsilanes under mild conditions. Mechanistic studies show the key intermediate and the order of bond migration involved in the process.
Article
Chemistry, Organic
Wen-Qing Zhu, Zi-Wei Zhang, Wen-Yong Han, Yu-Chen Fang, Ping Yang, Lin-Qiang Li, Yong-Zheng Chen
Summary: A novel palladium-catalyzed three-component reaction has been developed, which utilizes three different types of compounds to produce a range of new compounds in moderate to good yields. Significantly, aziridine was used as a vinylidene unit for the first time in the products.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Haibo Xu, Shengming Ma
Summary: An efficient method for synthesizing benzazocines through a double allene protocol has been developed. The reaction involves a highly selective palladium-catalyzed formal [6+2] annulation of allenyl benzoxazinanones with terminal allenes, resulting in the formation of challenging 8-membered cycles. The reaction exhibited decent yields, excellent regioselectivity, and remarkable Z-stereoselectivity for the exo-cyclic C=C bonds. The synthetic potential of benzazocine products has been demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Hongyu Guo, Sheng Zhang, Yang Li, Xiaoqiang Yu, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao
Summary: A palladium-catalyzed tail-to-tail reductive dimerization reaction of terminal alkynes is reported for the first time, leading to the efficient transformation of aromatic and aliphatic alkynes into 2,3-dibranched butadienes. The control of reaction solution acidity, achieved by a combination of pivalic acid and para-toluenesulfonic acid, is crucial for the selective tail-to-tail reductive dimerization reaction, which is proposed to proceed via a cationic alkenyl palladium intermediate under acidic conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ramaraju Korivi, Kanagaraj Madasamy, Popuri Sureshbabu, Subramaniyan Mannathan
Summary: An efficient and straightforward method for the synthesis of salicylanilide aryl and alkyl sulfonates from 1,2,3-benzotriazin-4(3H)-ones and organosulfonic acids is presented. The protocol is simple to perform and can be easily scaled up. It has a broad substrate scope with high tolerance towards functional groups, and provides the desired products in good to high yield. The application of the reaction is demonstrated by converting the desired product to salicylamides with high yields.
Review
Chemistry, Organic
Suven Das
Summary: This review summarizes recent advances (2018-2023) in the synthesis of indole skeletons via gold-catalyzed annulations of alkynes. Various types of alkynes, including ynamides, azido alkynes, ortho-alkynyl anilines, propargylic alcohols, ortho-alkynyl phenylimines, and miscellaneous alkynes, can be employed to afford various indole architectures under gold catalysis. Mechanisms are also included in most cases for a better understanding of the reaction pathway.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jingqiang Han, Huimin Yu, Weiwei Zi
Summary: This study reported a regioselective hydroarylation reaction of unactivated alkenes with aryl boronic acids directed by carboxylic acid. The reaction was achieved by using a homogeneous manganese catalyst MnBr(CO)(5) in the presence of KOH and H2O in the m-xylene reaction medium. Both internal and terminal alkenes showed good reactivity in this transformation, and a variety of functional groups were tolerated.
Article
Chemistry, Organic
Siti Nur Fairuz Binte Sheikh Ismail, Binmiao Yang, Yu Zhao
Summary: In this study, a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones was successfully achieved, leading to the construction of a novel spirocyclic tetrahydroquinoline scaffold with high stereoselectivity.
Article
Chemistry, Organic
Shangzhang Li, Yang Li, Riqian Zhu, Jin Bai, Yue Shen, Mengni Pan, Wanfang Li
Summary: A palladium-catalyzed reaction between [1,2,3]-benzotriazin-4(3H)-ones and DABAL-Me-3 was developed, leading to the formation of N-aryl amides derived from ortho-methylated carboxylic acids. Additionally, ortho-ethylation of [1,2,3]-benzotriazin-4(3H)-ones was achieved using triethylaluminum.
Review
Chemistry, Organic
Ben Niu, Yin Wei, Min Shi
Summary: In recent years, Pd-catalyzed annulation reactions using zwitterionic pi-allyl palladium intermediates have been extensively studied, demonstrating their importance in the synthesis of carbocyclic and heterocyclic compounds with potential pharmaceutical and biological applications. This review highlights the significant advances in organic synthesis based on zwitterionic pi-allyl palladium and propargyl palladium.
ORGANIC CHEMISTRY FRONTIERS
(2021)
