Shining Light on C−S Bonds: Recent Advances in C−C Bond Formation Reactions via C−S Bond Cleavage under Photoredox Catalysis

2020 ◽  
Vol 15 (22) ◽  
pp. 3637-3659
Author(s):  
Jian Gao ◽  
Jie Feng ◽  
Ding Du
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Photoredox Catalysis ◽  
Recent Advances ◽  
Bond Formation Reactions

scholarly journals Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 7051
Author(s):  
Lei Zhou
Keyword(s):  
Visible Light ◽  
Future Development ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Environmentally Benign ◽  
Personal Perspective ◽  
Photoredox Catalysis ◽  
Recent Advances ◽  
The Future ◽  
The Creation

The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional C-F bond formation methods. Visible light photoredox catalysis has been proven as an important and powerful tool for defluorinative reactions due to its mild, easy to handle, and environmentally benign characteristics. Compared to the classical C-F activation that proceeds via two-electron processes, radicals are the key intermediates using visible light photoredox catalysis, providing new modes for the cleavage of C-F bonds. In this review, a summary of the visible light-promoted C-F bond cleavage since 2018 was presented. The contents were classified by the fluorosubstrates, including polyfluorinated arenes, gem-difluoroalkenes, trifluoromethyl arenes, and trifluoromethyl alkenes. An emphasis is placed on the discussion of the mechanisms and limitations of these reactions. Finally, my personal perspective on the future development of this rapidly emerging field was provided.

Recent Advances on C-Se Bond-forming Reactions at Low and Room Temperature

2020 ◽  
Vol 23 (28) ◽  
pp. 3206-3225 ◽  
Author(s):  
Amol D. Sonawane ◽  
Mamoru Koketsu
Keyword(s):  
Room Temperature ◽  
Bond Formation ◽  
Bond Forming ◽  
Material Chemistry ◽  
Recent Advances ◽  
Bond Forming Reactions ◽  
Bond Formation Reactions

: Over the last decades, many methods have been reported for the synthesis of selenium- heterocyclic scaffolds because of their interesting reactivities and applications in the medicinal as well as in the material chemistry. This review describes the recent numerous useful methodologies on C-Se bond formation reactions which were basically carried out at low and room temperature.

Double C–H Activation for the C–C bond Formation Reactions

2018 ◽  
Vol 15 (7) ◽  
pp. 882-903 ◽  
Author(s):  
Jialin Liu ◽  
Xiaoyu Xiong ◽  
Jie Chen ◽  
Yuntao Wang ◽  
Ranran Zhu ◽  
...  
Keyword(s):  
Molecular Design ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Direct Functionalization ◽  
Catalyzed Reactions ◽  
Medium Ring ◽  
Bond Formation Reactions

Background: Among the numerous bond-forming patterns, C–C bond formation is one of the most useful tools for building molecules for the chemical industry as well as life sciences. Recently, one of the most challenging topics is the study of the direct coupling reactions via multiple C–H bond cleavage/activation processes. A number of excellent reviews on modern C–H direct functionalization have been reported by Bergman, Bercaw, Yu and others in recent years. Among the large number of available methodologies, Pdcatalyzed reactions and hypervalent iodine reagent mediated reactions represent the most popular metal and non-metal involved transformations. However, the comprehensive summary of the comparison of metal and non-metal mediated transformations is still not available. Objective: The review focuses on comparing these two types of reactions (Pd-catalyzed reactions and hypervalent iodine reagent mediated reactions) based on the ways of forming new C–C bonds, as well as the scope and limitations on the demonstration of their synthetic applications. Conclusion: Comparing the Pd-catalyzed strategies and hypervalent iodine reagent mediated methodologies for the direct C–C bond formation from activation of C-H bonds, we clearly noticed that both strategies are powerful tools for directly obtaining the corresponding pruducts. On one hand, the hypervalent iodine reagents mediated reactions are normally under mild conditions and give the molecular diversity without the presence of transition-metal, while the Pd-catalyzed approaches have a broader scope for the wide synthetic applications. On the other hand, unlike Pd-catalyzed C-C bond formation reactions, the study towards hypervalent iodine reagent mediated methodology mainly focused on the stoichiometric amount of hypervalent iodine reagent, while few catalytic reactions have been reported. Meanwhile, hypervalent iodine strategy has been proved to be more efficient in intramolecular medium-ring construction, while there are less successful examples on C(sp3)–C(sp3) bond formation. In summary, we have demonstrated a number of selected approaches for the formation of a new C–C bond under the utilization of Pd-catalyzed reaction conditions or hyperiodine reagents. The direct activations of sp2 or sp3 hybridized C–H bonds are believed to be important strategies for the future molecular design as well as useful chemical entity synthesis.

Recent Advances in Nitrogen–Nitrogen Bond Formation

Synthesis ◽  
2017 ◽  
Vol 49 (17) ◽  
pp. 3835-3847 ◽  
Author(s):  
Qihang Guo ◽  
Zhan Lu
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Pyrazole Derivatives ◽  
Triazole Derivatives ◽  
Synthetic Strategy ◽  
Recent Advances ◽  
Intermolecular Reactions ◽  
Nitrogen Bond

Over the last decade, N–N bond formation as a synthetic strategy has emerged as a powerful key step in the construction of highly valuable heterocycles from easily obtained materials. This review focuses on recent methods used to build N–N bonds, classified by intra- and intermolecular reactions with various types of N–X (O, C, N, H) bond cleavage.1 I ntroduction2 Intramolecular N–N Bond Formation2.1 Cleavage of N–O Bonds2.2 Cleavage of N–C Bonds2.3 Cleavage of N–N Bonds2.4 Cleavage of N–H Bonds2.4.1 Construction of Pyrazole Derivatives2.4.2 Construction of Triazole Derivatives2.4.3 Construction of Indazole and Pyrazoline Derivatives2.4.4 Construction of Other N–N Bond Derivatives3 Intermolecular N–N Bond Formation4 Conclusion

Remote C–C bond formation via visible light photoredox-catalyzed intramolecular hydrogen atom transfer

2020 ◽  
Vol 18 (24) ◽  
pp. 4519-4532 ◽  
Author(s):  
Hui Chen ◽  
Shouyun Yu
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Bond Formation ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Recent Advances ◽  
Intramolecular Hydrogen

Visible light photoredox catalysis combined with intramolecular hydrogen atom transfer (HAT) can serve as a unique tool for achieving remote C–C bond formation. Recent advances in photoredox-catalyzed remote C–C bond formation are summarized.

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