Article
Chemistry, Organic
Yue-Xiao Wu, Ming-Hui Huang, Kang Peng, Zhen Shi, Er-jun Hao, Zhi-Bing Dong
Summary: An iodine-catalyzed one-pot synthesis of benzoazole-substituted thioenamines was reported. The reaction proceeds through an electrophilic substitution pathway in a cross dehydrogenation coupling manner. The protocol is metal-free, easy to perform, tolerates various functional groups, and provides good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Beatriz Gonzalez-Saiz, Israel Carreira-Barral, Pablo Pertejo, Javier Gomez-Ayuso, Roberto Quesada, Maria Garcia-Valverde
Summary: The diastereoselective synthesis of two families of pyrrolopiperazine-2,6-diones is achieved through a novel one-pot reaction sequence. This method allows for the introduction of various substituents at the C4 position and the generation of a new stereogenic center on the bridgehead carbon (C8a) with high chemical yields and complete diastereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Benxiang Zhang, Jiayan He, Yang Gao, Laura Levy, Martins S. Oderinde, Maximilian D. Palkowitz, T. G. Murali Dhar, Michael D. Mandler, Michael R. Collins, Daniel C. Schmitt, Philippe N. Bolduc, Teyu Chen, Sebastian Clementson, Nadia Nasser Petersen, Gabriele Laudadio, Cheng Bi, Yu Kawamata, Phil S. Baran
Summary: Modern retrosynthetic analysis in organic chemistry is a method that guides the design of synthetic routes based on the polar relationships between functional groups. This approach assigns charges to functional groups and disconnects bonds between them. It has applications in undergraduate curriculum and synthetic methods, but requires careful considerations to overcome selectivity and oxidation state issues. In this study, a radical-based Ni/Ag-electrocatalytic cross-coupling of substituted carboxylic acids was reported, enabling a simplified approach to accessing complex molecular architectures.
Article
Chemistry, Organic
Xiao-De An, Zhonglin Wang, Yao-Bin Shen, Bin Qiu, Jian Xiao
Summary: A [6+1] annulation reaction was reported to construct a polycyclic 3,4-fused azepinoindole skeleton via cascade 1,6-hydridetransfer/cyclization. The newly designed 4-amino-indole-3-carbaldehyde was used as a six-atom synthon, reacting with arylamines and malononitrile to achieve the annulation reaction. The reaction proceeded smoothly under redox-neutral and metal-free conditions, providing a wide range of azepinoindoles in high yields with water as the only byproduct. Additionally, the methodology showcased high step- and atom-economy, highlighting its practicality.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wanjun Chen, Yaping Cheng, Tao Zhang, Yu Mu, Wenqi Jia, Guodu Liu
Summary: A nickel-catalyzed stereoselective asymmetric intramolecular reductive coupling of N-1,6-alkynones was reported, achieving efficient synthesis of versatile functionalized chiral pyrrolidines with high yields, excellent stereoselectivity, and enantioselectivity. The developed reaction is applicable to a broad substrate scope and can be scaled up to gram scale without loss of enantioselectivity. The study also investigated ligand effects and reaction mechanism, suggesting wider applications in organic synthesis and chemical biology, and potential for further explorations in new research fields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jie Ma, Xi Wang, Er-Jun Hao, Zhen Shi, Zhi-Bing Dong
Summary: An efficient synthesis method for 1,2-disubstituted indoles has been developed, providing a straightforward route to the target products from easily accessible starting materials. The protocol offers easy performance, high yield, and a broad substrate scope, indicating its potential synthetic value in the preparation of various biologically or pharmaceutically active compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Antonia Iazzetti, Dario Allevi, Andrea Calcaterra, Giancarlo Fabrizi, Antonella Goggiamani, Giulia Mazzoccanti, Alessio Sferrazza, Rosanna Verdiglione, Valeria Vergine
Summary: The gold-catalyzed cyclization of 2,2-bis(3-arylprop-2-yn1-yl)malonic acid efficiently produces substituted 3,8-dibenzyl-2,7-dioxaspiro[4.4]nonane-1,6-diones. The reaction occurs under mild conditions and yields the desired products in quantitative amounts with variously substituted starting materials. Additionally, the synthesis of gamma-arylidene spirobislactone with different substituents on the two aromatic rings has been achieved. This compound has significant relevance in pharmaceutical science due to the widespread presence of this scaffold in bioactive natural and synthetic products.
Article
Chemistry, Organic
Dakoju Ravi Kishore, Gedu Satyanarayana
Summary: This study presents an efficient and straightforward strategy for the synthesis of 2,3-disubstituted benzo[b]furans. The synthetic process involves a series of reactions, including a domino intermolecular coupling and intramolecular cyclization, resulting in a wide variety of compounds with good functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dhananjay Yadav, Maya Shankar Singh
Summary: A simple and efficient cascade approach for the synthesis of a series of 1,3-thiazinanes has been developed using beta-ketothioamide and epichlorohydrin in an intermolecular [3+3] heteroannulative coupling. This method offers several advantages, such as avoiding potential toxicity, easy work-up, and high yields, and it can be performed using readily available starting materials under transition-metal-free conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ryo Hikima, Aika Takeshima, Taichi Kano
Summary: Polysubstituted furans and pyrroles were synthesized in one-pot through coupling reactions and subsequent elimination reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Tao Wang, Ji-Xun Guan, Yun-Xuan Tan, Ping Tian
Summary: This paper reports the first cobalt-catalyzed highly selective arylation carbocyclization reaction of 1,6-allenynes with arylboronic acids. The reaction demonstrates moderate to high yields, broad substrate scope, and good compatibility with functional groups.
Article
Chemistry, Organic
Jivan Shinde, Veerababurao Kavala, Ching-Fa Yao
Summary: This research presents a selective palladium-catalyzed reaction for the addition of aryl boronic acids to propargyl 1,3-dicarbonyl alkyne without the need for water workup. The method shows high efficiency with a wide range of substrates using only 3 mol% [Pd] and a mild KOAc base. Furthermore, the application of this method in intramolecular cyclization and debenzoylation reactions leads to the synthesis of valuable trisubstituted pyran building blocks and (E)-4-methylene-1,6-diphenylhex-5-en-1-one.
Article
Chemistry, Organic
Kai-Xiang Feng, Cheng-Ke Tang, Qiao-Yu Shen, Ai-Bao Xia, Li-Sha Huang, Zhan-Yu Zhou, Xing Zhang, Xiao-Hua Du, Dan-Qian Xu
Summary: The catalytic diastereo- and enantioselective syntheses of C-2-symmetric axially chiral 1,4-dicarbonyl derivatives with 2,3-quaternary stereocenters were successfully achieved utilizing an organo-/iodine binary catalytic strategy. The reactions proceeded well under mild conditions without metals or strong bases.
Article
Chemistry, Organic
Hiroto Takahashi, Yuki Nagashima, Ken Tanaka
Summary: The electron-deficient bis(ethoxycarbonyl)-substituted cyclopentadienyl (Cp-E) rhodium(III) complex catalyzes the oxidative intramolecular 1,1-oxyamination of alkenes with N-benzoyl amino acids to produce oxazoloisoindole-2,5-diones. Experimental and theoretical mechanistic studies showed that this oxidative 1,1-oxyamination does not proceed through the aza-Wacker reaction, but involves the formation of a rhoda(III)oxazolidine initiated by carboxylic acid-directed N-H bond cleavage.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mengyan Duan, Guodong Hou, Yabiao Zhao, Congjun Zhu, Chuanjun Song
Summary: A facile strategy for synthesis of isoxazoles involving oxidation of propargylamines to oximes followed by CuCl-mediated cyclization has been developed. This protocol allows for construction of isoxazole cores with wide functional group compatibility, and can be successfully scaled up for gram-scale experiments and synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
