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.

Carbon-carbon bond-forming reactions using alkyl fluorides

2008 ◽  
Vol 80 (5) ◽  
pp. 941-951 ◽  
Author(s):  
Jun Terao ◽  
Hirohisa Todo ◽  
Hiroyasu Watabe ◽  
Aki Ikumi ◽  
Yoshiaki Shinohara ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Transition Metal Catalysts ◽  
Grignard Reagents ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Alkyl Fluorides ◽  
Bond Formation Reactions

This account reviews C-C bond formation reactions using alkyl fluorides mostly focusing on the transition-metal-catalyzed reactions. These reactions proceed efficiently under mild conditions by the combined use of Grignard reagents and transition-metal catalysts, such as Ni, Cu, and Zr. It is proposed that ate complex intermediates formed by the reaction of these transition metals with Grignard reagents play important roles as the active catalytic species. Organoaluminun reagents react directly with alkyl fluorides in nonpolar solvents at room temperature to form C-C bonds. These studies demonstrate the practical usefulness of alkyl fluorides in C-C bond formation reactions and provide a promising method for the construction of carbon frameworks employing alkyl fluorides. The scope and limitations, as well as reaction pathways, are discussed.

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.

scholarly journals Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2853-2866 ◽  
Author(s):  
Arkaitz Correa ◽  
Marcos Segundo
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Short Review ◽  
Great Promise ◽  
Coupling Reactions ◽  
Atom Economy ◽  
Bond Forming ◽  
Dehydrogenative Coupling ◽  
Peptide Derivatives

The functionalization of typically unreactive C(sp3)–H bonds holds great promise for reducing the reliance on existing functional groups while improving atom-economy and energy efficiency. As a result, this topic is a matter of genuine concern for scientists in order to achieve greener chemical processes. The site-specific modification of α-amino acid and peptides based upon C(sp3)–H functionalization still represents a great challenge of utmost synthetic importance. This short review summarizes the most recent advances in ‘Cross-Dehydrogenative Couplings’ of α-amino carbonyl compounds and peptide derivatives with a variety of nucleophilic coupling partners.1 Introduction2 C–C Bond-Forming Oxidative Couplings2.1 Reaction with Alkynes2.2 Reaction with Alkenes2.3 Reaction with (Hetero)arenes2.4 Reaction with Alkyl Reagents3 C–Heteroatom Bond-Forming Oxidative Couplings3.1 C–P Bond Formation3.2 C–N Bond Formation3.3 C–O and C–S Bond Formation4 Conclusions

Hierarchically porous covalent organic frameworks assembled in ionic liquids for highly effective catalysis of C–C coupling reactions

2020 ◽  
Vol 22 (8) ◽  
pp. 2605-2612 ◽  
Author(s):  
Jikuan Qiu ◽  
Huiyong Wang ◽  
Yuling Zhao ◽  
Pengxin Guan ◽  
Zhiyong Li ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Bond Formation ◽  
Catalytic Performance ◽  
Environmentally Benign ◽  
Coupling Reactions ◽  
Covalent Organic Frameworks ◽  
Hierarchically Porous ◽  
Highly Effective ◽  
Bond Formation Reactions

A simple and environmentally benign strategy was reported for the synthesis of hierarchically porous COFs in ionic liquids, and the obtained materials show highly effective catalytic performance for C–C bond formation reactions.

scholarly journals Bond Forming Reactions Involving Isocyanides at Diiron Complexes

Inorganics ◽  
2019 ◽  
Vol 7 (3) ◽  
pp. 25 ◽  
Author(s):  
Rita Mazzoni ◽  
Fabio Marchetti ◽  
Andrea Cingolani ◽  
Valerio Zanotti
Keyword(s):  
Transition Metal Catalysis ◽  
Organometallic Complexes ◽  
The Other ◽  
Coupling Reactions ◽  
Molecular Fragments ◽  
Carbene Ligands ◽  
Metal Catalysis ◽  
Bond Forming ◽  
Environmental Friendly ◽  
Catalyzed Reactions

The versatility of isocyanides (CNR) in organic chemistry has been tremendously enhanced by continuous advancement in transition metal catalysis. On the other hand, the urgent need for new and more sustainable synthetic strategies based on abundant and environmental-friendly metals are shifting the focus towards iron-assisted or iron-catalyzed reactions. Diiron complexes, taking advantage of peculiar activation modes and reaction profiles associated with multisite coordination, have the potential to compensate the lower activity of Fe compared to other transition metals, in order to activate CNR ligands. A number of reactions reported in the literature shows that diiron organometallic complexes can effectively assist and promote most of the “classic” isocyanide transformations, including CNR conversion into carbyne and carbene ligands, CNR insertion, and coupling reactions with other active molecular fragments in a cascade sequence. The aim is to evidence the potential offered by diiron coordination of isocyanides for the development of new and more sustainable synthetic strategies for the construction of complex molecular architectures.

Formation of Carbon-Nitrogen Bond Mediated by Hypervalent Iodine Re-agents Under Metal-free Conditions

2020 ◽  
Vol 24 ◽  
Author(s):  
Yaxin O Yang ◽  
Xi Wang ◽  
Jiaxi Xiao ◽  
Yadong Li ◽  
Fengxia Sun ◽  
...  
Keyword(s):  
Building Blocks ◽  
Review Article ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Metal Free ◽  
Bond Forming ◽  
The Past ◽  
Oxidative Coupling Reactions ◽  
Nitrogen Bond

: In the past several decades, hypervalent iodine chemistry has witnessed prosperous development as hypervalent iodine reagents have been widely used in various organic transformations. Specifically, hypervalent iodine reagents have been vastly used in various bond-forming reactions. Among these oxidative coupling reactions, the reactions involving the formation of C-N bond have been extensively explored to construct various heterocyclic skeletons and synthesize various useful building blocks. This review article is to summarize all the transformations in which carbon-nitrogen bond formation occurred by using hypervalent iodine reagents under metal-free conditions.

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.

scholarly journals Dimethylisosorbide (DMI) as a Bio-Derived Solvent for Pd-Catalyzed Cross-Coupling Reactions

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2293-2297 ◽  
Author(s):  
Allan Watson ◽  
Kirsty Wilson ◽  
Jane Murray ◽  
Helen Sneddon ◽  
Craig Jamieson
Keyword(s):  
Chemical Industry ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Heck Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions

Palladium-catalyzed bond-forming reactions, such as the ­Suzuki–Miyaura and Mizoroki–Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalyzed reactions: Suzuki–Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47–91% yield), and Sonogashira (12 examples, 65–98% yield).

Transition-metal-free and base promoted C–C bond formation via C–N bond cleavage of organoammonium salts

2021 ◽  
Author(s):  
Tao Zhang ◽  
Kunyu Wang ◽  
Yuting Ke ◽  
Yuanyuan Tang ◽  
Long Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Ammonium Salts ◽  
Metal Free ◽  
Bond Forming ◽  
Benzyl Ammonium

A transition-metal-free and base promoted C–C bond forming reaction of benzyl C(sp3)-H bond with organoammonium salts via C–N bond cleavage has been reported. Benzyl ammonium salts as well as cinnamyl...

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