Photoinduced Alkenylation of Alkenyl Sulfones with EDA Complexes between NHPI Esters and HE
Wiley Online Library » Asian Journal of Organic Chemistry
by Mingli Xu, Chenyue Zhao, Yongxiang Huang, Shuo Hu, Dongping Cheng, xiaoliang xu
5d ago
A novel alkenylation reaction between N-hydroxyphthalimide (NHPI) esters and alkenyl sulfones is reported. It undergoes the formation of electron donor-acceptor (EDA) complex and a series of alkenes are obtained in good to excellent yields. It has the advantages of simple operation, mild reaction conditions, and metal-free ..read more
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Approach to Spirocyclohexadienes via Visible Light‐Mediated ipso‐Cyclization of Amino Acid Derivatives with N‐(2‐Phenyl)benzoyl Groups
Wiley Online Library » Asian Journal of Organic Chemistry
by Yuki Yoshida, Haruka Takeuchi, Norihito Arichi, Shinya Oishi, Hiroaki Ohno, Shinsuke Inuki
5d ago
Spirocycles are important structural motifs, found in natural and pharmaceutical compounds, which have attracted considerable interest in modern drug discovery research. Herein, we describe the development of a visible light-mediated ipso-cyclization of amino acid derivatives with N-(2-phenyl)benzoyl groups, allowing easy access to a variety of spirocyclohexadienes. The addition of water was found to be beneficial in promoting the reaction progress. Investigation of the substrate scope revealed that incorporating an electron-donating moiety at the 3'-position of the biphenyl group resulted in ..read more
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Methanesulfonic Acid‐Catalyzed Friedel‐Crafts Alkylation: Towards Sustainable Synthesis of Arylalkanes from Donor–Acceptor Cyclopropane Ketones
Wiley Online Library » Asian Journal of Organic Chemistry
by Lakshmi Goswami, Sayantan Paul, Ajay G. Mamale, Rajesh G. Gonnade, Asish K. Kumar Dr. Bhattacharya
1w ago
We present herein Brønsted acid-catalyzed Friedel-Crafts alkylation of phenols with Donor–Acceptor cyclopropane ketones. The presence of the 1,4-diphenyl butan-1-one and 1,3-diphenyl propane-1-one motifs in various naturally occurring biologically significant molecules inspired us to pursue the direct synthesis of these structural frameworks. Utilizing methanesulfonic acid (MeSO3H) as a catalyst, we achieved a more environmentally friendly and high-yielding synthesis, owing to its cost-effectiveness, biodegradability, transition-metal and additives free conditions. Furthermore, we have success ..read more
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Construction of polymers with highly dispersed reactive phases and open pores for catalyzing the efficient synthesis of CO2 to α‐methylene cyclic carbonates
Wiley Online Library » Asian Journal of Organic Chemistry
by Xiaoxuan Guo, Zhixiu Yang, Fenglei Zhang, Lijing Gao, Ruiping Wei, Guomin Xiao
1w ago
Selective capture of carbon dioxide as a C1 feedstock for the preparation of high-value chemicals has been recognised as an important way to mitigate the crisis. In this work, a new heterogeneous catalyst, Cu@CP-PII, was developed through the rational construction of an open-pore organic skeleton, which is easy to synthesise and highly efficient. With the synergistic effect between the high CO2 affinity of the porous skeleton and the highly dispersed Cu(I) sites of the activated alkynes, it can be used for the efficient preparation of α-methylene cyclic carbonates at ambient temperature and pr ..read more
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Palladium‐Catalyzed Carbonylation of Aryl Sulfonium Salts with CO2 as a CO Surrogate
Wiley Online Library » Asian Journal of Organic Chemistry
by Yanhui Guo, Li Wei, Huanfeng Jiang, Chaorong Qi
2w ago
Palladium-catalyzed carbonylation of aryl sulfonium salts with CO2 as a CO surrogate has been successfully developed via a one-pot two-step procedure. Thus, by merging thianthrenation and the carbonylation, site-selective aromatic C–H carbonylation of a plethora of readily available arenes can be realized with CO2, providing access to a variety of structurally diverse and useful benzamides, esters and carboxylic acids. Simple operation, broad substrate scope, good functional group tolerance and mild reaction conditions are the attractive features of the method. Late-stage functionalization of ..read more
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Hypervalent Iodine Mediated Synthesis of 2‐Aminobenzazoles and 2‐Aminobenzothiazoles
Wiley Online Library » Asian Journal of Organic Chemistry
by Yi Gu, Yao-Dong Li, Ye Ge, Jiang-Long Huang, Huajin Xu, Yi Hu
2w ago
The hypervalent iodine mediated, silica gel promoted synthesis of 2-aminobenzazoles and 2-aminobenzothiazole derivatives under metal-free mild conditions within short time (30min) has been developed. Under this process, PhI(COOCF3)2 (PIFA) or PhI(COOCH3)2 (PIDA) acts as an oxidant and radical initiator direct activated the ortho-C-H bond of substrate, silica gel as weakly lewis acid effectively increased the reactivity of the reaction system. This method is compatible with various of arylurea and arylthiourea substrates, which is green, efficient, simple to operate and ..read more
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Methyl‐ and Methoxy‐substituted 2‐(Pyridin‐2‐yl)‐4‐(4‐aminophenyl)quinazolines: Synthesis and Photophysical Properties
Wiley Online Library » Asian Journal of Organic Chemistry
by Alexandra E. Kopotilova, Maria I. Valieva, Ekaterina A. Kudryashova, Ekaterina S. Starnovskaya, Tatyana N. Moshkina, Emiliya Vladimirovna Nosova, Olga S. Taniya, Alexey A. Kalinichev, Alexander S. Novikov, Dmitry S. Kopchuk, Pavel A. Slepukhin, Valery N. Charushin
2w ago
A series of 2-(2-pyridyl)quinazoline luminophores containing donor aryl fragment at position 4 and methyl or methoxy groups at benzene ring has been synthesized by efficient three-step route. The linear optical properties have been studied by UV/Vis absorption and photoluminescence spectra in two solvents. We revealed that introduction of additional methyl group or the replacement of methyl substituents with methoxy ones lead to sequentially shift of absorption and emission maximum to blue region. 9H-Carbazol-9-yl-containing derivative is characterized by hypsochromically shifted absorpti ..read more
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Metal‐free stereoselective synthesis of tetrahydropyrans bearing adjacent quaternary and tertiary stereocenters by acid mediated cyclization
Wiley Online Library » Asian Journal of Organic Chemistry
by Carlos Díez-Poza, Patricia Val, Enol López, Asuncion Barbero
2w ago
A convenient route for the preparation of tetrahydropyran (THP) derivatives with a quaternary and tertiary vicinal stereocenters is reported. The atom economy acid-catalyzed cyclization of allylsilyl alcohols provided polysubstituted tetrahydropyrans in good yields and excellent diastereoselectivities (>95:5). In comparison with the traditional oxymercuration procedure, this approach resulted to be more efficient in both yield and stereocontrol ..read more
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Metal‐Free [2 + 3] Dipolar Cycloaddition/Denitration Cascade between Nitroalkenes and α‐Diazoesters: Regioselective Access to Functionalized NH‐Pyrazoles
Wiley Online Library » Asian Journal of Organic Chemistry
by Ganesh Kumar, Subhasish Ray, Satyen Saha, Maya Shankar Singh
2w ago
An efficient one-pot synthesis of 1H-pyrazoles has been realized via cascade cyclocondensation of β-nitroalkenes as C2 synthon with α-diazoesters as C1N2 unit. The reaction proceeds via concomitant formation of two new (C-N & C-C) bonds in one stretch leading to ethyl 5-nitro-4-phenyl-4,5-dihydro-3H-pyrazole-3-carboxylate intermediate, which undergoes base mediated denitration enabling the formation of NH-pyrazoles. This protocol not only features easy operation, catalyst-free conditions, good to high yields, wide scope and late-stage functionalization, but also opens up a new avenue for s ..read more
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Reactions of Diaminonaphthalenes with a Cage‐Opened C60 Derivative
Wiley Online Library » Asian Journal of Organic Chemistry
by Guanglin Huang, Shumpei Sadai, Yoshifumi Hashikawa, Yasujiro Murata
2w ago
The reactions of cage-opened C60 derivatives with aromatic diamines are known to cause an orifice-enlargement in association with incorporating extended π-systems. The present work focuses on 1,2-, 2,3-, and 1,8-diaminonaphthalenes for the synthesis of a series of naphthalene-fused fullerene derivatives. For the former two, orifice enlargement proceeded by cleaving two C=C bonds to afford an opening with a ring-atom count of 20, in which the naphthalene moiety was fused by a pyrazine ring. For the reaction with 1,8-diaminonaphthalene, only one C=C bond was cleaved to give a 17-membered-ring op ..read more
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