Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

2011 ◽  
Vol 111 (3) ◽  
pp. 1596-1636 ◽  
Author(s):  
Irina P. Beletskaya ◽  
Valentine P. Ananikov
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Cross Coupling ◽  
Addition Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Transition-metal-catalyzed reactions of carbon-heteroatom bond formation by substitution and addition processes

2005 ◽  
Vol 77 (12) ◽  
pp. 2021-2027 ◽  
Author(s):  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Triple Bond ◽  
Bond Formation ◽  
Cross Coupling ◽  
Addition Reactions ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Two types of transition-metal-catalyzed cross-coupling reactions, which both lead to the formation of carbon-heteroatom bonds, are considered: RX + E-H and E-X + RM. The potential of addition reactions of E-H or E-E to double or triple bond in C-E bond formation is also demonstrated.

Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3714-3734
Author(s):  
Zhi-Bing Dong ◽  
Jin-Quan Chen
Keyword(s):  
Transition Metal ◽  
Nucleophilic Addition ◽  
Cross Coupling ◽  
Addition Reactions ◽  
Nucleophilic Additions ◽  
Coupling Reactions ◽  
Organometallic Reagents ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractOrganometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years.Introduction1 Transition-Metal-Catalyzed Cross Couplings Involving Organo­zinc Reagents2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents3 Transition-Metal-Free Cross Couplings Involving Zn and Mg ­Organometallic Reagents4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics6 Conclusion

scholarly journals Recent Advances in Transition-Metal-Catalyzed, Directed Aryl C–H/N–H Cross-Coupling Reactions

Synthesis ◽  
2017 ◽  
Vol 49 (20) ◽  
pp. 4586-4598 ◽  
Author(s):  
Martyn Henry ◽  
Mohamed Mostafa ◽  
Andrew Sutherland
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Short Review ◽  
Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Amination and amidation of aryl compounds using a transition-metal-catalyzed cross-coupling reaction typically involves prefunctionalization or preoxidation of either partner. In recent years, a new class of transition-metal-catalyzed cross-dehydrogenative coupling reaction has been developed for the direct formation of aryl C–N bonds. This short review highlights the substantial progress made for ortho-C–N bond formation via transition-metal-catalyzed chelation-directed aryl C–H activation and gives an overview of the challenges that remain for directed meta- and para-selective reactions.1 Introduction2 Intramolecular C–N Cross-Dehydrogenative Coupling2.1 Nitrogen Functionality as Both Coupling Partner and Directing Group2.2 Chelating-Group-Directed Intramolecular C–N Bond Formation3 Intermolecular C–N Cross-Dehydrogenative Coupling3.1 ortho-C–N Bond Formation3.1.1 Copper-Catalyzed Reactions3.1.2 Other Transition-Metal-Catalyzed Reactions3.2 meta- and para-C–N Bond Formation4 C–N Cross-Dehydrogenative Coupling of Acidic C–H Bonds5 Conclusions

Developments in Organocatalyzed C(Ar)- C(Ar) Bond formation Reactions via Single Electron Transfer Mechanism: An Overview

2021 ◽  
Vol 08 ◽  
Author(s):  
Lalit Yadav ◽  
Sandeep Chaudhary
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Metal Free ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: The formation of new bonds through C-C bond formation is of utmost importance in the synthesis of biologically privileged scaffolds and therapeutic drugs. In recent years, extensive efforts has been done to improve the intermolecular and intramolecular cross-coupling reaction in the simple, mild, efficient, economical, and eco-friendly manner via transition metal-free or organocatalytic direct C-H bond activation methodology. The traditional crosscoupling era continuously shifted to metal-free, organocatalytic, or metal-free cross-dehydrogenative coupling strategies to fast-track the reactions and diminishing the typical purification processes. Therefore, recent advances on the transitionmetal-free, organocatalytic inter- and intra-molecular cross-coupling reactions have been introduced and discussed in the present article. In view of the reaction mechanism, organocatalytic cross-coupling reactions undergo through the radical pathways, radical anionic intermediate which is completely different from traditional transition metal-catalyzed reactions. The exploration of transition metal-free organocatalyzed cross-couplings for direct C-H arylation of arenes has grown significantly, thereby, improving the formation of a wide range of aryl-aryl /aryl-heteroaryl/ heteroaryl-heteroaryl compounds. In the survey, transition metal-free/organocatalytic cross-coupling reactions showed a higher efficiency under simple and mild conditions than the comparative transition metal-catalyzed cross-coupling reactions. However, the higher regioselectivity and chemoselectivity are still far ahead in organocatalytic cross-coupling reactions due to their specific intrinsic mechanistic pathway. The tuning of many parameters such as oxidative states, ligands coordination, and counter anions, etc., which results in the specific direct C-H functionalization with flexible methodology are missing in the transition metal-free cross-coupling reactions. The highly systematic transition metal-catalyzed chemistry is still playing a dominant role over transition metal-free chemistry in organic synthesis. The organocatalyzed transition-metal-free conditions should be more efficient, chemoselective, and regioselective for further potential development and applications in organic synthesis. For the endless pursuit of sustainable chemistry and green chemistry, such transition-metalfree/organocatalytic reactions should be never ceased. Additional curious attention and interest have been developed so far, and chemists are showing their eagerness and talents to uncover the hidden treasure of green chemistry. In this review article, we highlighted the developments of various transition metal-free/organocatalytic C-H bond activation reactions which further encourages the advancement in the development of sustainable C-C coupling reactions and their further applications towards the synthesis of biologically privileged scaffolds and drug molecules.

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