Transition metal-free C-3 functionalization of quinoxalin-2(1H)-ones: recent advances and sanguine future

2021 ◽  
Author(s):  
Kiran ◽  
Payal Rani ◽  
Sandhya Chahal ◽  
Jayant Sindhu ◽  
Sudhir Kumar ◽  
...  

A gradual shift from metal-catalyzed to metal-free methods is occurring, as the latter are more environmentally benign. This review discusses sustainable protocols for the construction of C–C, C–N, C–P, C–S, and C–O bonds via C–H functionalization of quinoxalin-2(1H)-ones.

Synthesis ◽  
2021 ◽  
Author(s):  
Leonid Fershtat ◽  
Fedor Teslenko

Five-membered heterocyclic N-oxides attracted special attention due to their strong application potential in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are constantly required. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are briefly summarized. Main routes to transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. Transformation patterns of the hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.


2017 ◽  
Vol 15 (2) ◽  
pp. 285-300 ◽  
Author(s):  
K. Kubota ◽  
H. Iwamoto ◽  
H. Ito

Recent advances in borylations of organic halides, including both transition-metal-catalyzed and metal-free methods are summarized. Borylative cyclization is also discussed.


2021 ◽  
Author(s):  
Guoxue He ◽  
Jinyu Ma ◽  
Jianhui Zhou ◽  
Chunpu Li ◽  
Hong Liu ◽  
...  

A facile method access to indanones was developed under metal- and additive-free conditions in which L-proline served as efficient and environmentally benign catalysts. Compared with previous indanones synthesis by transition-metal-catalyzed...


Synthesis ◽  
2017 ◽  
Vol 50 (02) ◽  
pp. 193-210 ◽  
Author(s):  
Egor Verbitskiy ◽  
Gennady Rusinov ◽  
Oleg Chupakhin ◽  
Valery Charushin

Data spanning the period 2000–2017 on the direct C–H functionalization of pyrimidines are collected and discussed in this review. This demonstrates the surge of interest and creativity that this field of chemistry has experienced during the last two decades. Plausible applications of highly functionalized pyrimidines are also discussed.1 Introduction2 Transition-Metal-Catalyzed C–H Functionalization of Pyrimidine Derivatives3 Transition-Metal-Free Direct C–H Functionalization of Pyrimidine Derivatives4 Deprotonative Metalation of Pyrimidine Derivatives5 Conclusions


Author(s):  
Timofey D. Moseev ◽  
Mikhail V. Varaksin ◽  
Denis A. Gorlov ◽  
Valery N. Charushin ◽  
Oleg N. Chupakhin

This review highlights the recent advances in the functionalization of polyfluoro(aza)aromatics via both transition metal-catalyzed and metal-free C–C coupling reactions for the period from 2006 to the beginning of 2021.


Molecules ◽  
2019 ◽  
Vol 24 (1) ◽  
pp. 164 ◽  
Author(s):  
Fei Zhao ◽  
Pinyi Li ◽  
Xiaoyan Liu ◽  
Xiuwen Jia ◽  
Jiang Wang ◽  
...  

The addition of amide/sulfonamide bonds to alkynes is not only one of the most important strategies for the direct functionalization of carbon–carbon triple bonds, but also a powerful tool for the downstream transformations of amides/sulfonamides. The present review provides a comprehensive summary of amide/sulfonamide bond addition to alkynes, including direct and metal-free aminoacylation, based-promoted aminoacylation, transition-metal-catalyzed aminoacylation, organocatalytic aminoacylation and transition-metal-catalyzed aminosulfonylation of alkynes up to December 2018. The reaction conditions, regio- and stereoselectivities, and mechanisms are discussed and summarized in detail.


Synthesis ◽  
2021 ◽  
Author(s):  
Xin-Ge Yang ◽  
Xue-Qiang Wang ◽  
Shen-Huan Li ◽  
Cheng-Yu Long

AbstractRecently, intense efforts have been dedicated to the development of novel synthetic strategies to access aromatic amines due to their importance in the pharmaceuticals, agrochemicals, materials, and natural product areas. Although numerous transition-metal-catalyzed C–N formation strategies have been described for the preparation of aromatic amines in the past few decades, complementary methods under transition-metal-free conditions are still required. We present the recent advances in the exploration of innovative amination approaches via C(sp2)–O/C(sp2)–S bond cleavage in this review.1 Introduction2 Stoichiometric Base-Promoted Amination3 Base-Catalyzed Amination4 Photoredox-Catalyzed Amination5 Acid-Promoted Amination6 Conclusion and Perspectives


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