Recent Advances in Photocatalytic C–N Bond Coupling Reactions

Synthesis ◽  
2020 ◽  
Author(s):  
Wing-Yiu Yu ◽  
Chun-Ming Chan ◽  
Yip-Chi Chow
Keyword(s):  
Carbonyl Compounds ◽  
Bond Formation ◽  
Coupling Reactions ◽  
Amino Groups ◽  
Cyclization Reactions ◽  
Radical Coupling ◽  
Synthetic Intermediates ◽  
Photocatalytic Reactions ◽  
Metal Catalyzed ◽  
Pharmaceutical Agents

Catalytic C–N bond formation is one of the major research topics in synthetic chemistry owing to the ubiquity of amino groups in natural products, synthetic intermediates and pharmaceutical agents. In parallel with well-established metal-catalyzed C–N bond coupling protocols, photocatalytic reactions have recently emerged as efficient and selective alternatives for the construction of C–N bonds. In this review, the progress made on photocatalytic C–N bond coupling reactions between 2012 and February 2020 is summarized.1 Introduction1.1 General Mechanisms for Photoredox Catalysis1.2 Pioneering Work2 C(sp2)–N Bond Formation2.1 Protocols Involving an External Oxidant2.2 Oxidant-Free Protocols3 C(sp3)–N Bond Formation3.1 Direct Radical–Radical Coupling3.2 Addition Reactions to Alkenes3.3 Reductive Amination of Carbonyl Compounds3.4 Decarboxylative Amination4 Cyclization Reactions4.1 C(sp2)–N Heterocycle Formation4.2 C(sp3)–N Heterocycle Formation5 Other Examples6 Conclusion and Outlook

Transition-Metal-Catalyzed Annulative Coupling Cascade for the Synthesis of 3-Methyleneisoindolin-1-ones

Synthesis ◽  
2020 ◽  
Vol 52 (06) ◽  
pp. 807-818 ◽  
Author(s):  
So Won Youn
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Short Review ◽  
Coupling Reactions ◽  
Cyclization Reactions ◽  
One Pot ◽  
Bond Forming ◽  
Wide Range ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This short review describes the recent progress made on transition-metal-catalyzed annulative couplings for the synthesis of 3-methyleneisoindolin-1-ones, which are useful intermediates for the synthesis of numerous alkaloids and can be often found in a wide range of natural products and pharmaceuticals. In particular, new one-pot multiple C–C/C–N bond-forming processes for the construction of the 5-methylenepyrrol-2-one nucleus of such compounds are summarized.1 Introduction2 Intramolecular Cyclization Reactions: C3–N or C3–C3a and C–C Bond Formation3 Intermolecular Annulative Coupling Reactions3.1 C3–C3a and C3–N Bond Formation3.2 C1–C7a and C3–N Bond Formation3.3 C1–C7a and C1–N Bond Formation3.4 C1–C7a, C1–N and C3–N Bond Formation3.5 C3–C3a, C1–C7a, C1–N and C3–N Bond Formation: A Pd-Catalyzed One-Pot Sonogashira Coupling–Carbonylation–Amination–Cyclization Cascade4 Conclusion

scholarly journals Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 861 ◽  
Author(s):  
Ha-Eun Lee ◽  
Dopil Kim ◽  
Ahrom You ◽  
Myung Hwan Park ◽  
Min Kim ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Chiral Ligand ◽  
Catalytic Systems ◽  
Carbon Bond ◽  
Carbonyl Derivatives ◽  
Carbon Carbon Bond ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.

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

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.

Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds

2006 ◽  
Vol 78 (2) ◽  
pp. 209-214 ◽  
Author(s):  
Lutz Ackermann ◽  
Robert Born ◽  
Julia H. Spatz ◽  
Andreas Althammer ◽  
Christian J. Gschrei
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phosphine Oxides ◽  
Aryl Chlorides ◽  
Catalytic Activation ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Metal Catalyzed

Studies on the use of easily accessible heteroatom-substituted secondary phosphine oxides as preligands for cross-coupling reactions are described. These air-stable sterically hindered phosphine oxides allow for efficient palladium-catalyzed Suzuki- and nickel-catalyzed Kumada-coupling reactions using electronically deactivated aryl chlorides. In addition, they enable nickel-catalyzed coupling reactions of magnesium organyls with aryl fluorides at ambient temperature, and ruthenium-catalyzed coupling reactions of aryl chlorides via C-H bond activation. Finally, the application of modular diamino phosphine chlorides as preligands for a variety of transition-metal-catalyzed C-C and C-N bond formation reactions employing electron-rich aryl chlorides is presented.

Recent Developments on Denitrogenative Functionalization of Benzotriazoles

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3781-3800
Author(s):  
Guobing Yan ◽  
Vinod K. Tiwari ◽  
Jie Yu ◽  
Anoop S. Singh ◽  
Jian Yu
Keyword(s):  
Short Review ◽  
Structural Motif ◽  
Easy Access ◽  
Coupling Reactions ◽  
Future Perspectives ◽  
Cyclization Reactions ◽  
Recent Developments ◽  
Synthetic Routes ◽  
Metal Catalyzed ◽  
Benzotriazole Derivatives

AbstractBenzotriazoles are employed as useful synthons in organic synthesis, and due to their unique structural motif, they are able to undergo denitrogenation during the construction of new bonds. Various methods for the functionalization of benzotriazoles as precursors of ­ortho-amino arenediazoniums have recently been developed that involve transition-metal-catalyzed coupling reactions, mainly via cyclization, borylation, alkenylation, alkylation, carbonylation and the formation of carbon–heteroatom bonds. In this short review, we primarily focus on the recent applications of benzotriazoles in organic chemistry that proceed via a denitrogenative process, and the mechanisms are also discussed.1 Introduction2 Common Synthetic Routes Allowing Easy Access to Benzotriazole Derivatives3 Formation of C–C Bonds3.1 Cyclization Reactions3.2 Arylation, Alkenylation, Alkylation and Carbonylation Reactions4 Carbon–Heteroatom Bond Formation5 Miscellaneous Denitrogenative Functionalization6 Conclusions and Future Perspectives

Recent Developments in Photochemical and Electrochemical Decarboxylative C(sp3)–N Bond Formation

Synthesis ◽  
2020 ◽  
Vol 52 (09) ◽  
pp. 1357-1368 ◽  
Author(s):  
Lifang Tian ◽  
Yahui Wang ◽  
Yue Zheng ◽  
Xiaoqing Shao ◽  
Velayudham Ramadoss
Keyword(s):  
Rapid Development ◽  
Bond Formation ◽  
Short Review ◽  
Toxic Substances ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Drug Molecules ◽  
Recent Developments ◽  
Metal Catalyzed ◽  
Nitrogen Containing Compounds

Considering the important applications of nitrogen-containing compounds in agrochemical materials and biomolecular drug molecules, research on methods for the construction of C–N bonds quickly and efficiently has become an important topic in synthetic chemistry. Carboxylic acids are inexpensive, stable, and non-toxic substances that are widely present in Nature, which makes them appealing as potential coupling partners for C(sp3)–N bond-forming reactions. Moreover, compared with the well-established transition-metal-catalyzed protocols, the rapid development of photoredox catalysis and electrochemical methods in recent years provides options for chemists to design new synthetic routes. In this short review, we concentrate on the decarboxylative C(sp3)–N coupling reactions mediated by visible light or electricity, with special attention on mechanistic insights.1 Introduction2 Photoredox-Mediated Decarboxylative C(sp3)–N Bond Formation2.1 Intramolecular Decarboxylation2.2 Intermolecular Decarboxylation3 Electrochemistry-Induced Decarboxylative C(sp3)–N Bond Formation3.1 Intramolecular Decarboxylation3.2 Intermolecular Decarboxylation4 Conclusions and Outlook

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