Article
Chemistry, Multidisciplinary
Yuki Yamamoto, Akiya Ogawa
Summary: The cycloaddition reaction of o-diisocyanoarenes with interelement compounds under light enables the synthesis of bisphosphinated quinoxalines through the radical cyclization pathway, elucidating the reaction mechanism and product selectivity. Additionally, the reaction of diphosphines with isocyanides having o-functional groups provides further insights into the bisphosphination process. Furthermore, the one-pot synthesis of Pd-II-quinoxaline complex is achieved through this developed reaction.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Thikhamporn Uppalabat, Anyawan Tapdara, Onnicha Khaikate, Thanapat Worakul, Panida Surawatanawong, Pawaret Leowanawat, Darunee Soorukram, Vichai Reutrakul, Jatuporn Meesin, Chutima Kuhakarn
Summary: A highly efficient synthesis of indolo[3,2-c]quinolines and benzothieno[3,2-c]quinolines has been developed using o-alkynyl-N-phenylformamide derivatives as substrates. The reaction proceeds through a tandem process involving POCl3-assisted intramolecular cyclization of o-alkynylisocyanobenzenes, leading to the desired products in moderate to high yields. The synthesized products can be further modified, and the photophysical properties of selected indolo[3,2-c]quinolines were characterized and explained using time-dependent DFT calculations.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Panyi Huang, Zhiyang Yan, Jiaxin Ling, Peixuan Li, Jiayang Wang, Jianjun Li, Bin Sun, Can Jin
Summary: A metal- and catalyst-free visible light-driven carbon-carbon bond-forming cyclization cascade has been reported. The cascade is initiated by the direct homolysis of C-sp3-Br under visible light, generating a transient alkyl radical intermediate and forming a series of 3-substituted chroman-4-ones. This work demonstrates a facile and effective strategy for constructing three-dimensional polycyclic compounds using two-dimensional long-chain compounds as building blocks.
Article
Chemistry, Organic
Jin Wang, Haitao Liu, Yaohui Liu, Wanting Hao, Yingqi Yang, Yanan Sun, Xianxiu Xu
Summary: An efficient and environmentally friendly aerobic radical cascade reaction has been developed for the synthesis of a diverse range of 2-thio-substituted quinolines using o-vinylphenylisocyanides and thiols, without the need for additional catalysts or oxidants. Mechanistic investigations revealed that the reaction is initiated by a thiyl radical generated under aerobic conditions, which then undergoes radical annulation with a vinyl substituent.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Hua-Hua Wang, Hui Shao, Guanglong Huang, Jianqiang Fan, Wai-Pong To, Li Dang, Yungen Liu, Chi-Ming Che
Summary: In this study, chiral iron porphyrin complexes were found to catalyze the asymmetric intramolecular C(sp(3))-H amination of aryl and arylsulfonyl azides, providing chiral indolines and benzofused cyclic sulfonamides, respectively. The reactions exhibited high enantioselectivity (up to 93% ee) and high yields (up to 99%) under mild conditions with 410 nm light.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jiaqi Li, Shichong Wang, Jingjing Zhao, Pan Li
Summary: A visible light-promoted radical-mediated ring-opening/cyclization of vinyl benzotriazoles has been developed for the synthesis of functionalized phenanthridines from alkyl bromides. The readily available and bench-stable vinyl benzotriazoles serve as valuable alternative radical acceptors during the synthesis of phenanthridines.
Article
Chemistry, Multidisciplinary
Patrick J. Deneny, Roopender Kumar, Matthew J. Gaunt
Summary: The incorporation of the fluoromethyl group into organic molecules can significantly affect their physicochemical properties and offer a promising strategy for the discovery of novel pharmaceutical agents. A new method for direct fluoromethylation of unfunctionalized C(sp(2)) centres using commercially available fluoroiodomethane has been developed, demonstrating the synthesis of complex fluoromethylated products through a radical chain process.
Article
Chemistry, Multidisciplinary
Palani Natarajan, Partigya, Pooja
Summary: A novel blue LED-induced method for synthesizing a variety of compounds has been developed without the need for a photoredox catalyst. This method offers advantages such as environmental friendliness, mild conditions, scalability, absence of toxic solvents/additives, and absence of transition metals.
NEW JOURNAL OF CHEMISTRY
(2022)
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
Bruce A. L. Sacchelli, Bianca C. Rocha, Leandro H. Andrade
Summary: An ultrafast methodology utilizing microwave irradiation was employed for the first time to construct novel highly functionalized 2-quinolinones from N-(o-ethynylaryl)-acrylamides (1,7-enynes). The method involved six key consecutive reactions, including a diastereoselective step, to achieve good overall yield of 2-quinolinone-fused gamma-lactones (up to 46%; 10 s).
Article
Chemistry, Organic
Thomas Rigotti, Thorsten Bach
Summary: This study presents a visible light-driven approach for the synthesis of Bicyclo[2.2.1]hexanes, and shows the possibility of further functionalization through consecutive reactions.
Article
Chemistry, Organic
Atena B. Solea, Sining Wang, Xiao-Song Xue, Aurelien Crochet, Katharina M. Fromm, Kendall N. Houk, Olimpia Mamula, Christophe Allemann
Summary: This study describes a straightforward one-pot method for synthesizing unreported pyrido-[2,1-a]isoindolones in excellent yield, along with the synthesis and full characterization of two novel isoindolones. The alkyl substituents on the pyridine were found to play a crucial role in determining the reaction outcome. The mechanism, investigated through DFT calculations, reveals a novel intramolecular cyclization reaction involving a carboxylic acid activated by tosyl chloride and an electron-poor pyridinic nitrogen.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Jinhuan Dong, Lei Wang, Haoyue Li, Xinrong Leng, Xiaoyu Guo, Zhongyan Hu, Xianxiu Xu
Summary: A new method for solvent-dependent chemoselective Morita-Baylis-Hillman-type self-cyclization and dimerization of o-alkenyl arylisocyanides was developed, providing concise access to various 3-acylquinoline and pyrrolo[1,2-a:3,4-b ']diindole frameworks via distinct domino processes from the same starting materials.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Chao Li, He Wang, Lu Liu, Ran Sun, Xin Wang, Ming-Dong Zhou, Lei Li
Summary: A novel base-catalyzed intramolecular self-cyclization reaction has been developed for the synthesis of 4-cyano-3-arylquinolines. This method offers a general, efficient, and atom-economic approach with a wide range of substrates and excellent functional group compatibilities.
Article
Chemistry, Organic
Navin Yadav, Sushil Ranjan Bhatta, Jarugu Narasimha Moorthy
Summary: This study demonstrates a visible light-mediated synthesis of hetero-arenes (isoquinolines, benzothiazoles, and quinazolines) through the use of isocyanides and inexpensive acyl peroxides. It is the first time that singlet-excited isocyanides have been shown to decompose acyl peroxides into aryl/alkyl radicals. The resulting radicals attack isocyanides, leading to the formation of imidoyl radicals which subsequently cyclize to generate heteroarene products. The protocol eliminates the need for external photocatalysts, oxidants, additives, and bases.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
