Recent Advance on Benzofuranones: Synthesis and Transformation via C-H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Zhi Tang ◽  
Zhou Tong ◽  
Shuang-Feng Yin ◽  
Nobuaki Kambe ◽  
Renhua Qiu
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Efficient Synthesis ◽  
Bond Functionalization ◽  
Pka Value ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Benzofuranone is a sort of important skeleton in many fields, such as natural products, pharmaceuticals, building blocks, antioxidants and dyes. Their efficient synthesis and transformations have attracted great attentions in organic synthesis. They can be synthesized by Friedel−Crafts reaction, intramolecular dehydration ring-closing reaction and transition-metal-catalyzed reaction, etc. And their direct utilization to prepare other functional molecules enhances their further application. Due to their low pKa value and easy enolization ability, the transformation of benzofuranones via C(3)-H bond functionalization is a hot issue in the last ten years. Herein, we highlight the advances on the synthesis of benzofuranones and its transformation via C-H functionalization. Some of other transformations related to benzofuranones are also referred in this review.

Transition-metal-catalyzed ortho-selective C−H functionalization reactions of free phenols

2021 ◽  
Author(s):  
So Won Youn ◽  
Cheon-Gyu Cho
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Functional Materials ◽  
Building Blocks ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Synthetic Transformations

Phenols are important readily available chemical feedstocks and versatile synthetic building blocks for diverse synthetic transformations. Their motifs are prevalent in a diverse array of natural products, pharmaceuticals, functional materials,...

Recent Advances in Transition-Metal-Catalyzed C–H Addition to Nitriles

Synthesis ◽  
2021 ◽  
Author(s):  
Wei-Wei Liao ◽  
Shu-Qiang Cui
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Recent Progress ◽  
Building Blocks ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Forming ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed C–H bond addition to nitriles has emerged as a powerful synthetic approach for the construction of C–C bonds in organic synthesis. Due to the merits of atom- and step-economy, as well the easy availability of the starting materials, these transformations not only deliver acyclic aryl ketone products with nitriles­ as C-building blocks, but can also be utilized for the highly efficient­ assembly of azaheterocyclic skeletons using nitriles as C–N building blocks. This short review summarizes recent progress on transition-metal-catalyzed C–C bond-forming reactions based on C(sp2)–H and C(sp3)–H additions to nitriles.1 Introduction2 Palladium-Catalyzed C–H Addition to Nitriles2.1 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Ketone (Imine) Products2.2 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Azaheterocycles2.3 Palladium-Catalyzed C–H Addition to Nitriles/1,2-Rearangement3 Other Transition-Metal-Catalyzed C–H Additions to Nitriles4 Summary and Outlook

scholarly journals Photo-induced copper-catalyzed sequential 1,n-HAT enabling the formation of cyclobutanols

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Zhusong Cao ◽  
Jianye Li ◽  
Guozhu Zhang
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Copper Complex ◽  
Building Blocks ◽  
Hydrogen Atom Transfer ◽  
Efficient Synthesis ◽  
Bond Functionalization ◽  
Cascade Cyclization

AbstractCyclobutanols are privileged cyclic skeletons in natural products and synthetic building blocks. C(sp3)−H functionalization is a prolonged challenge in organic synthesis. The synthesis of cyclobutanols through double C(sp3)-H bond functionalization remains elusive. Here we report the efficient synthesis of cyclobutanols through intermolecular radical [3 + 1] cascade cyclization, involving the functionalization of two C − H bonds through sequential hydrogen atom transfer. The copper complex reduces the iodomethylsilyl alcohols efficiently under blue-light irradiation to initiate the tandem transformation. The mild reaction tolerates a broad range of functional groups and allows for the facile generation of elaborate polycyclic structures.

C–H functionalization of quinazolinones by transition metal catalysis

2020 ◽  
Vol 18 (24) ◽  
pp. 4497-4518 ◽  
Author(s):  
Prasanjit Ghosh ◽  
Bhaskar Ganguly ◽  
Sajal Das
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Important Class ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Quinazolinone and its derivatives are an important class of heterocyclic scaffolds in pharmaceuticals and natural products. This review provides the recent research advances in the transition metal catalyzed selective C–H bond functionalization of quinazolinone.

scholarly journals Trihaloethenes as versatile building blocks for organic synthesis

2016 ◽  
Vol 14 (24) ◽  
pp. 5377-5389 ◽  
Author(s):  
Adriana S. Grossmann ◽  
Thomas Magauer
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Trihaloethenes are versatile C2-building blocks that can be simply modified via addition, elimination and transition metal-catalyzed reactions.

Regioselective Transition-Metal-Catalyzed C–H Functionalization of Anilines

Synthesis ◽  
2018 ◽  
Vol 50 (14) ◽  
pp. 2693-2706 ◽  
Author(s):  
Jamie Leitch ◽  
Christopher Frost
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Building Blocks ◽  
Synthetic Methodology ◽  
Biologically Relevant ◽  
The Subject ◽  
Transition Metal Catalyzed ◽  
Biologically Relevant Molecules ◽  
Metal Catalyzed

Anilines are a vital synthetic core of pharmaceuticals, agrochemicals, natural products and building blocks. Metal-catalyzed C–H functionalization has emerged as a powerful tool to derivatize biologically relevant molecules. To this end, the derivation of anilines via catalytic C–H functionalization has been the subject of important new synthetic methodology. This review focuses on the tactics used to allow regioselective C–H functionalization of anilines.1 Introduction2 ortho-Selective C–H Functionalization2.1 Palladium2.2 Rhodium2.3 Ruthenium2.4 Nickel3 meta-Selective C–H Functionalization4 para-Selective C–H Functionalization5 Conclusion

Copper Catalysts in the Synthesis of Five-membered N-polyheterocycles

2018 ◽  
Vol 15 (7) ◽  
pp. 940-971 ◽  
Author(s):  
Navjeet Kaur
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Copper Catalysts ◽  
Research Field ◽  
Chemoselective Synthesis ◽  
Specialized Equipment ◽  
Transition Metal Catalyzed ◽  
Synthetic Methodologies ◽  
Metal Catalyzed ◽  
Traditional Approaches

Background: Due to significant biological activity associated with N-, O- and S-heterocycles, a number of reports for their synthesis have appeared in recent decades. Traditional approaches require expensive or highly specialized equipment or would be of limited use to the synthetic organic chemist due to their highly inconvenient approaches. This review summarizes the applications of copper catalysts with the emphasis on their synthetic applications for nitrogen bearing polyheterocylces. In summary, this review article describes the synthesis of a number of five-membered poly heterocyclic rings. Objective: Nowadays new approaches that employ atom-economical and efficient pathway have been developed. The researchers are following natural models to design and synthesize heterocycles. The transition metal catalyzed protocols have attracted the attention as compared to other synthetic methodologies because they use easily available substrates to build multiple substituted complicated molecules directly under mild conditions. In organic synthesis, constituted by transition metal catalyzed coupling transformations are one of the most powerful and useful protocols. The N-heterocycles are synthesized by this convenient and useful tool. Conclusion: The efficient and chemoselective synthesis of heterocycles by this technique has appeared as an important tool. This review shows a highly dynamic research field and the employment of copper catalysts in organic synthesis. Several strategies have been pointed out in the past few years, to meet more sustainable, efficient and environmentally benign chemical products and procedures. The catalytic strategies have been the focus of intense research because they avoid the use of toxic reagents. Among these catalytic strategies, highly rewarding and an important method in heterocycles synthesis is metal catalyzed synthesis.

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