Article
Chemistry, Multidisciplinary
Toshimichi Ohmura, Yuta Takaoka, Michinori Suginome
Summary: The copper-catalyzed silafunctionalization of alkynes using silylboronic ester as a silicon source has made rapid progress. The trans-selective 1,2-addition of silylboronic esters to internal arylalkynes was efficiently promoted by the CuOt-Bu/RCy2P/NaOt-Bu catalysts, with a stereochemical switch to cis-addition observed in reactions utilizing Me-2(i-PrO)Si-B(pin) in hydrocarbon solvents including cyclohexane.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Kunlayanee Punjajom, Sureeporn Ruengsangtongkul, Jumreang Tummatorn, Praneet Paiboonsombat, Somsak Ruchirawat, Charnsak Thongsornkleeb
Summary: A general protocol for oxidative annulation was developed to prepare 2-methyl-3,4-diacylquinolines directly from 2-alkynylanilines and 1,3-ketoesters. The reactions were mediated by Mn(OAc)3 in acetic acid at room temperature, leading to the desired quinoline products in one-pot in low to good overall yields on a wide range of substrates. The current method is convenient, conducted under mild conditions, and has short reaction times.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Yuan Yang, Dilver Pena Fuentes, Xiao-Feng Wu
Summary: Carbonylation reactions are important in contemporary organic chemistry as they provide access to compounds with carbon monoxide or methyl groups. We report a copper-catalyzed carbonylative catenation and borylation reaction and propose a possible reaction mechanism.
Article
Chemistry, Multidisciplinary
Jonathan H. Boyce, Benjamin J. Reisman, Brian O. Bachmann, John A. Porco
Summary: This study reports novel rearrangements of acylphloroglucinols mediated by formic acid to access diverse synthetic acylphloroglucinol scaffolds, with insights on the mechanism provided by Density-functional theory (DFT) analysis. Evaluation of products using multiplexed activity profiling (MAP) identified SASs that suppressed pS6 (Ser235/236) markers of mTOR and ERK signaling pathways activation. These results demonstrate the pharmacological potential of novel chemotypes through biomimetic synthesis and multiplexed activity profiling.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Liangliang Song, Lingchao Cai, Erik V. Van der Eycken
Summary: This minireview outlines the recent developments of microwave-assisted post-Ugi reactions for the synthesis of polycycles, where diverse polycycles are prepared in an efficient, rapid, and step-economical manner through transition metal-catalyzed or transition metal-free transformations.
Review
Biochemistry & Molecular Biology
Younghoon Kim, Sandip Sengupta, Taebo Sim
Summary: The review discusses the anti-tumor activities and synthetic routes of natural and synthetic lactones, highlighting their potential as anticancer agents and aiming to advance the process of oncology drug discovery based on natural products.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Review
Biochemistry & Molecular Biology
Alicja K. Surowiak, Lucyna Balcerzak, Stanislaw Lochynski, Daniel J. Strub
Summary: Terpenoids with lactone moieties are known for their high bioactivity, with artemisinin being a well-known drug against malaria. New terpenoid lactones are considered potential active agents against various diseases.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Multidisciplinary
Meng Li, Ruixue Zhang, Qiushan Gao, Huanfeng Jiang, Ming Lei, Wanqing Wu
Summary: Herein, a direct and efficient synthesis of diverse polysubstituted fused tetracyclic heterocycles with good functional group tolerance from diarylalkynes under different palladium catalytic systems is presented. The unprecedented intermolecular nucleopalladation of diarylalkynes through the highly selective sequential double insertion of isocyanide was achieved for the first time in this study. The practicality of this method was further demonstrated by the construction of various bioactive molecules and important structural motifs, with potential applications in materials science and biochemistry. In addition, density functional theory calculations revealed an interesting Pd walk during the cyclization process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
James E. Baumann, Gojko Lalic
Summary: A new method for the differential dihydrofunctionalization of terminal alkynes has been developed, enabling the synthesis of allylic boronate esters through a reductive three-component coupling reaction. This transformation, promoted by a copper/palladium catalyst system, hydrofunctionalizes both pi-bonds of the alkyne. The method is compatible with a wide range of functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Naoki Ishida, Yoshiki Kamae, Keigo Ishizu, Yuka Kamino, Hiroshi Naruse, Masahiro Murakami
Summary: The system described in the passage utilizes solar energy to capture, store, and release chemical energy for hydrogenation. Through a two-step process, solar energy is converted into chemical energy, which is then used for hydrogenation, with the advantage of easy recovery and reuse.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Nerea Conde, Maria Teresa Herrero, Garazi Urgoitia, Raul SanMartin
Summary: Metal-catalyzed cascade processes based on hydrofunctionalization of alkynes have the potential to provide advantageous approaches to otherwise synthetically challenging compounds. A CNN pincer palladium(II) complex, acting as a homogeneous catalyst, provides the corresponding polyheterocycles with a higher substrate/catalyst ratio.
Article
Chemistry, Multidisciplinary
Zijun Huang, Yudong Li, Jiaxing Zhou, Yi Zhang, Jiacheng Wu, Yongkai Wu, Fan Zhang, Zhengjun Fang, Yuehui Li
Summary: In this study, a palladium-catalyzed carbonylation reaction using CO2 and waste hydrosilane PMHS was developed for the synthesis of aurones from terminal aromatic alkynes and 2-iodophenols. Various terminal alkynes and substituted 2-iodophenols were efficiently converted to the corresponding aurones. The mechanistic investigation suggests that the silyl formate derived from CO2 and PMHS plays a crucial role in the carbonylation reaction.
Article
Chemistry, Organic
Ketema Alemayehu Asserese, Hanmin Huang
Summary: A novel palladium-catalyzed cascade hydrocarbonylation followed by intramolecular spirolactonization of 2-vinylaryl hydroxyalkyl ketones has been developed, providing high yields and high chemoselectivities of oxaspirolactones. This method is compatible with various functional groups and uses commercially available catalyst components under mild reaction conditions.
Article
Chemistry, Organic
Stephane Golling, Pierre Hansjacob, Nassim Bami, Frederic R. Leroux, Morgan Donnard
Summary: This paper reports a palladium-catalyzed annulation reaction that can synthesize polysubstituted amino-indenones, with different regioselectivity observed between different ynamides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Li-Wen Zhan, Chuan-Jun Lu, Jia Feng, Ren-Rong Liu
Summary: This study reports for the first time that palladium compounds can catalyze the hydroarylation of 1-alkynylindoles with organoborons, resulting in the synthesis of chiral C-N atropisomers. The reaction conditions are mild and lead to excellent regio-, stereo- (Z-selectivity), and enantioselectivity. The simplicity, high stereoselectivity, and good functional group tolerance of this catalytic system make it highly attractive.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
